123: How leaving a fortune 500 company led to the creation of a successful travel and lifestyle blog with Jackie Shields.
On this week’s episode, I speak with Jackie Shields who is a lifestyle blogger and the founder of getlostwithjackie.com
Jackie had an amazing career working for a Fortune 500 company but decided she needed to stop working for other people’s dreams in order to pursue her own.
So, she left her steady job and dove into the unknown to start her own business and to create the now successful blog Get Lost With Jackie, where she shares travel and lifestyle content.
Listen on to find out how Jackie has been able to use her knowledge in business to create a successful travel and lifestyle blog.
Listen Below:
Show Notes:
Debbie:
Hey everyone, thank you so much for joining us today. I’m so excited to be here with Jackie. Hey Jackie, how are you?
Jackie:
Hi guys, I’m doing great. How are you?
Debbie:
I am great. Thank you so much for being here with us. I’m so excited to talk to you, Jackie. So, Jackie and I actually met on a cruise ship with Royal Caribbean. That was so much fun with you and the girls.
Jackie:
That was a really fun trip. I like working with cruises there. Anything Caribbean, hey, you got me.
Debbie:
You and I got to talking and I learned so much from you. So, we’re going to talk about all of your incredible journey. Before we do that, can you tell us a little bit more about you and why you live an offbeat life?
Jackie:
I’m Jackie and I run my travel blog called Get Lost With Jackie which I kind of started from a happy accident. I didn’t have any intentions of starting a blog or starting a travel advice business or travel brand by any means. I’ve just started an Instagram page to feature some of my photos from traveling and I think in my true entrepreneurial spirit when I noticed that you can monetize Instagram and you can monetize your passions outside of a business forum, it was just something that I had to do. It was something that I wanted to do, that I was called to do and now I love it. It’s been six years since I started Get Lost With Jackie and about three or four years since I started monetizing it. I would say about a year and a half since I’ve been making a livable wage off of it and I think that being able to take that passion and turn it into a business is what helped me to lead my offbeat life for sure.
Debbie:
It’s amazing that you were able to do this and you actually live off of this now. This is your main bread and butter, but how were you able to actually leave your nine to five to dive into this full time? What was that moment like for you?
Jackie:
I actually left my nine to five 10 years ago on July 6 and I was working for a car dealership group here on Long Island in New York. It’s a big company, it has a lot of respect but I did not like it. I didn’t like the politics, I didn’t like that management was favored even when they were doing terrible things. Fast forward 10 years between the Me Too movement and the lack of tolerance now for people abusing their power, I don’t think that the scenario would have been the same if I had gone to HR and said, “Hey, I’m not really digging this manager style”. He’s threatening us and things of that sort, that my concerns would have been taken a little bit more seriously.
Jackie:
And after about six months of what I would call mental abuse, I just could not take it anymore. I quit and I had no idea what I was going to do. I just knew that it was bigger than that BMW dealership and that job that I had there. And when you know in your heart that what you have in store for you is bigger than BMW, I feel like you have to go and chase after that. So, I just started helping a few of my friends. One of my friends had their own car dealership, it was a small used car dealership. He was selling five to 10 cars a month and I started helping him with some marketing, a little bit with some web copy. And then, another friend of mine, she was a makeup artist, she asked me if I could help her create a website and help her with describing her services and what she could do.
Jackie:
After helping them too, I realized that what I had was a business in itself – assisting small businesses. So, I started my first company in 2000. May 25th of 2011, I legally formed the company, it was called Smooth Startup. I assisted people with consulting for just about every stage of the startup process; from business planning to organization, to setting up internal processes, setting up internal documents to make sure that cashflow is on point. I just kinda fell and tripped into consulting and I love it. To this day I still do consulting on the side and it’s something that I feel like I will always do. It also did give me the opportunity to become location independent and to travel more even before I started Get Lost With Jackie. Smooth Startup gave me the financial means and the freedom to go wherever I wanted to go and to do whatever I wanted to do. That’s something I don’t think you can trade for the world.
Debbie:
Absolutely. And sometimes we are placed in situations where there’s really nowhere to go but out because you really should not be in that type of situation. You had the courage to finally say, “I will not stand for this.” And even though you don’t know what your future is going to be like, maybe where your money is going to come in, it’s going to be a lot better than where you are at that moment. So, that is incredible that you were able to do that, Jackie. So, you started that company, you have a business background because of that and you knew how to handle being able to be an entrepreneur because that’s really a lot of our struggles when we first go into this as a solar entrepreneur or even a freelancer, it’s just being able to handle this when we’re on our own. How did you transition from managing your business before to becoming a travel entrepreneur? Was that smooth transition or was it pretty rough?
Jackie:
It was definitely rough. It’s definitely still can be rough. I have learned that I, personally, am someone who craves routine which is something that you don’t often get when you’re on the road or in a different hotel or in a different country every night. Even though with Smooth Startup, I was technically able to be location independent. I still had an office, I still went into work at my desk every day. And making that shift from working at a desk with your dedicated Wifi that you know is going to work to working in hotels on Spotty Wifi that takes hours to upload or download things. That was very difficult for me. I lost contracts, I lost money, I lost clients, I doubted myself. I can’t tell you how many times I said, “This is the last trip I’m going on. I can’t do this anymore.”
Jackie:
For me, it was just about finding the way that it worked for me. Like I’ve said before, I need that routine which is hard to find. So, I just set in certain places the things that I could do every single morning. So, I would start my morning with coffee, I write down at least three things that I’m grateful for. And then, I either workout or stretch. Most often I just stretch and I saved my workout for later but just a little bit of moment, just to keep myself in a routine. So, what might go on after those first three steps of my morning could be completely different every day in every place. But just keeping that routine helped me to stay sane in a way and finding things that you can do anywhere in the world and create kind of like a similar life no matter what country you’re in or what state you’re in was really pivotal for me.
Debbie:
Absolutely. I think that’s one of the things that we don’t think about when we leave our nine to five is that we still should create some sort of a routine for ourselves because then you become all over the place and you don’t know what to do with yourself.
Jackie:
It really makes me get burned out.
Debbie:
Absolutely. You’re kind of just like a chicken without a head. You’re going all over the place and you don’t know what is happening with yourself. So, that is such a good idea to do that and sometimes we forget to do it, but it’s so crucial having that routine daily.
Jackie:
100%.
Debbie:
When you were transitioning to all of these different things, first from your nine to five then to your business as a consultant and now as a traveling entrepreneur with your blog and also with social media, did you ever have a “what now?” moment? I had that, I’m sure you’ve had that too. What was that like for you?
Jackie:
I feel like I have that almost daily. It’s been hard because you chase a dream for so long that when you finally achieve it, you expect to have like a big celebration or $1 million in the bank. There are all these stereotypes that come with the idea or the illusion of success. And I think that realizing for me that my ultimate form of success does not have to do with a monetary amount in the bank or a list of achievements or goals or awards or anything like that. But just truly being able to wake up in the morning and say, “I’m happy” is my greatest success. When I wake up happy every day, you almost feel guilty about it. You’re supposed to work hard, you’re supposed to work 10, 12, 18-hour days. And what happens when you’re able to make a living only working two to three hours a day, you have all this free time and you feel guilty about it. Your free time to go sit on the beach on a Tuesday and you’re doing it and “I should be doing something else” is what we think. So for me, the “now what?” became a way of “now, how do I program my mind to work differently than the way that we’ve been told it should work?”
Debbie:
That is such a great point, Jackie, because I think we do. We have that sense of guilt whenever we’re not working the way people think we should be working. And I’m in a similar boat as you because when you have created a system for your business and you have other people working for you, you kind of tend to try to find more work for yourself. All of those hours that you used to put on it is gone and now you’re like, “What do I do with myself? Okay, I need to find more work for myself. I need to do this, I need to do that.” And sometimes it’s just learning that you need to embrace it.
Jackie:
Exactly. Embrace the free time you worked for this. I think that’s something else is we forget what we’re working for and ultimately everyone works to retire. And what if you can have an early retirement? Society creates these ideas of the way things should look and I feel like the deprogramming of those ideas, especially when we’re self employed, no one became self employed to follow the rules of the nine to five. So, I feel like it’s just about deprogramming and writing your own rules and truly being unapologetic because anyone else’s opinions of how you’re living your life are completely irrelevant to you. It has nothing to do with you. I feel like just making sure that you’re happy with yourself every day is your main goal.
Jackie:
And also, especially in self employment, if you’re happy with the work you’re doing, you’re happy with the salary you’re receiving, what else do you need?
Debbie:
It’s definitely that deep programming of yourself because of what you think is expected of you. That is a really hard thing to do, believe it or not, because you do have that guilt or you will get pushed back from people and it’s definitely a different type of mindset and you will get a lot of support from people who are in a similar field or in a similar mindset as you. Also, finding that community can be really helpful.
Jackie:
It’s especially important. A lot of times, I’m not sure for you but for me, let’s say the trailblazer in the family, I’m the first member of my family to kind of create their own path and not stick to a union job or a government job.
Jackie:
I come from a lot of blue collar workers and I love them so much and truthfully, I don’t think I could be the person I am today without seeing all these people around me with such outstanding work ethic and every day going to work and doing the job they need to do to support their families and things of that sort. But at the end of the day, you can’t compare work ethic from someone who’s working a nine to five to work ethic of someone who is self-employed because it’s hard to understand, unfortunately. If you’re surrounded by people who are living, let’s say a traditional life or working a traditional job, it’s very hard to have those people that you know and love, understand the path you’re on. So, finding your community and people that you can bounce ideas off of and people that just understand your ups and downs is crucial. And thankfully the Internet makes it very easy to find people who have similar interests. It’s an interesting world we live in but, like how you’ve mentioned it, it’s so important to have support from people who understand what your journey is.
Debbie:
And I think for my listeners, I have talked about this several times about creating that community and almost every single one of my guests, I have really emphasized that it’s just finding those people that you can really bounce ideas off of and have that support. And you’re right, there’s just a difference, right? There’s a difference from your mindset and what other people’s mindsets are when they have a nine to five to what you actually have – a business. It’s a completely different game, a different monster to tackle. And we don’t realize that until we are in that battle and we get really creative and there’s a lot of things that you have to do that you have never encountered before. So, it’s very crucial to have that. Now. Jackie, when you left your nine to five, you had challenges, right? Like a lot of misgivings probably and a lot of doubts. But what about now that you actually have this business that you have, what are your current challenges in your business and how do you find the ways to solve them?
Jackie:
One of the biggest challenges I have now is leveling up. I’m very comfortable. Like I’ve said, two to three hours of work a day is very comfortable. How can I level my brand up? How can I level my voice up? What else can I do to amplify not only myself but also my brand. I would like create video series and I’m just now getting into video and it’s extremely intimidating. So, I think staying on top of it is also about throwing yourself back out of that comfort zone. Because when you get too comfortable, it’s not to say that you can’t make a good living, it’s not to say that you can’t make decent money, you can’t work on good projects, but at some point you’re gonna crave that change the same way that I craved the shift out of nine to five.
Jackie:
Right now, I’m craving a shift out of what I’ve become comfortable in my works. My daily work life has been very comfortable. So, I’m just thinking about different content I can create. I actually just moved and just in the whole redoing my place process, I’m thinking about what content can I create here that has nothing to do with travel. It’s a completely different realm from what I know. I think that just making sure that you’re comfortable but not too comfortable is definitely where you need to find a good balance and still continue to, like I’ve said, level up.
Jackie:
I guess to throw yourself into your work again, but in a different completely different way. For me, that’s with video work, I’m throwing myself into this unknown, but it is still kind of familiar because it’s my brand now. It’s not completely unknown to me.
Debbie:
Definitely. I think it’s just that I find that people who are entrepreneurs, we always have to be in some way or form challenged. And when you are no longer challenged, you become very bored. You need to find something else to get that creativity flowing. And if you don’t have that, then again, you’re back in the same place even though you’re making money because essentially it’s not about money anymore because you are doing that now. It’s about excitement and challenging yourself again and making yourself better. Whether it is to create something new, learning something new, finding other ways to really express yourself and do all of those things.
Jackie:
Yes, totally. I actually just started painting. It has nothing to do with my brand or any work that I’m going to put out, but just something different to express my creativity differently. And I feel like that’s something else, a lot of people… whether you’re in nine to five, self-employed, whatever it is, we get so caught up in life that we forget about the simple pleasures and kind of honing in on your childlike innocence. For me, just painting, I was just painting like lines, it’s not even anything life-changing but it felt good and it got my mind thinking differently. And I feel like you’ve said, “challenging yourself, putting yourself back out there” is super important, especially if you’re self-employed and you have to keep yourself going.
Debbie:
Yeah. And I love that you said, “It doesn’t even have to be anything that would work. It’s just pleasure, it’s just simple pleasure.” And I think we forget that sometimes we don’t need to do anything for a purpose of anything except for joy, right? Honestly, that’s been underrated. Just doing nothing, even though it doesn’t serve a purpose, even though like it doesn’t have to do with anything, it’s just gives you joy and happiness. I think we all need that in our life.
Jackie:
We definitely do.
Debbie:
Now, Jackie, you travel quite often When I do travel quite often it does become overwhelming and oftentimes it gets really lonely, right? Because now we don’t have any coworkers with us, we’re often in new places. How is that for you? Have you experienced loneliness when you are on the road?
Jackie:
I definitely have and it is difficult to deal with especially if you’re halfway around the world and you’re 12 hours ahead or 12 hours behind of your time at home so, you can’t even call home and expect to hear those familiar voices. I think, for me, a big part of being able to stay away for a long time, travel for a long time and not succumb to that loneliness was figuring out how to sit with that loneliness and not let it bother you because it’s kind of like when someone tells you to feel the emotions and it’s okay to cry kind of thing. It’s okay to feel lonely especially if you’re alone. And I feel like it goes into these stereotypes where people maybe make us feel that we shouldn’t feel those feelings.
Jackie:
“You shouldn’t feel lonely. You shouldn’t allow yourself to be sad on the road. You’re living a beautiful dream life.” But the fact of the matter is I’m human and I’m someone who’s always been surrounded by people. So, for me, to not feel lonely abroad would almost be weird. When I do feel lonely, I have a playlist on my phone it’s called “take me home” and it’s just all songs from my childhood or songs that remind me of people that I know. and love. And it takes me back to a place where I don’t feel lonely anymore. It can be anything, for some people maybe looking at videos of their nieces and nephews or a picture with their family. I feel like everyone can have something that can just remind them of the good times and for me, I can always come home.
Jackie:
I feel like just knowing that I’m not away forever, I’m not in outer space, it’s not impossible for me to get home and just kind of coming back down to reality and looking at the facts. The facts of the matter are; I’m living a dream life and I get to go home when this trip is over or I get to see my friends when this stage of my life ends. I’m just kind of trying to speak to myself realistically about that loneliness.
Debbie:
Giving yourself that pep talk every now and then when you’re feeling that. Now, Jackie. One of the things that people really wonder about before they go into a new lifestyle or if they’re leaving a nine to five is how much money do they need to save before they set off to be location independent. How much did you actually spend before you felt comfortable in leaving that job or the business that you had and how were you able to budget your money so that it can last?
Jackie:
I’m going to be 100% honest with you guys. I still have not learned how to budget my money. I’m 31 years old and it is still a work in progress. Thankfully, for me, my dad instilled in me like, “You want to have good credit.” So, it was very conflicting to come from a blue collar worker who told me, “your credit is your lifeline,” and then, every single entrepreneur ever told me that “you’re not a good entrepreneur if your credit isn’t crap.” I had no plan financially, I didn’t put money aside. I actually quit my job on a complete whim and I didn’t have any intention of starting a business. I was even going to ask my employer to relocate me to another dealership but I ultimately decided that, that wasn’t my best plan.
Jackie:
I can take this from Elizabeth Gilbert’s book, it’s called “Big Magic”. She said that even after she published “Eat. Pray. Love.” and even after it was picked up for a movie that she was still serving as a waitress. And I feel like the number one thing, if you’re entering into entrepreneurship or you’re starting a business, creating a business around your passion, that you want to ensure that you have another source of income that has nothing to do with your creativity, your artwork, your passions, et cetera. I learned this the hard way. I wish I had read this advice ages ago. But I kept my money in my business and there were some times where I had to decide do I want to pay this bill or do I want to have money to go out this weekend?
Jackie:
I’m down to my last $250, and what do I do with it? Do I pay my stuff on time? I don’t know when my next paycheck is. So, I think that if I had had a job like waitressing or something on the side that would have just supplemented the income to pay for my bills so that I wasn’t paying for my life with the money that I was making in my business. I feel like that was a big mistake I made, I didn’t know any better and I still struggle with it. I’m still on net 90 with some contracts and I’m sometimes borrowing from my personal savings to pay things for the business or I’m borrowing things from the business to pay my personal bills. So, I feel like it’s going to be a constant struggle until I am way beyond financially. I also don’t think that there’s a definitive number that you can put on it like, “oh, you need $5,000 aside if you want to start your own business,” ’cause you truthfully can start a business with no money and you can also start that business while still working elsewhere. I probably would have stayed at that job I hated that paid me very well if I had known the struggle with two years after that.
Debbie:
Well I think you know what, even though it’s a really hard lesson to learn, you remember it so much more when you make those mistakes. Not to say that you should do that. I mean, it’s definitely better to learn from other people’s mistakes instead of learning it the hard way. And I think now there’s a lot of mentality for people to just leave and quit their job and just go off and travel and not have a plan. And even though it has worked out for a lot of people, it shouldn’t be your first and only option because you’re gonna struggle either way. If you do that, you’re gonna struggle. If you don’t do that, you stay at your job and you’re working at another passion project, you’re struggling. So, you’re struggling either way, it’s just the pill that you want to take. So, make sure you think about it before you dive into it. Now, Jackie, let’s forward to 50 years from now and you’re looking back at your life. What legacy would you like to leave and what do you want to be remembered for?
Jackie:
I want to be remembered for helping people to live unapologetically themselves. I’ve actually been talking about the next phase of my life, the next phase of my business and my brand and where do I want to go from here? And truthfully, I feel that a lot of people live for other people, whether it’s their parents, which thankfully I have parents that know that I am my own person and they don’t try to dictate who I am or what I do. Even sometimes people live for spouses or siblings and we’re all very concerned with what other people think. We sometimes forget what we think, what do we think about ourselves? How do we feel about ourselves? And that’s something I feel like I want to help people understand that this is your life, your journey.
Jackie:
You only get one shot at this. Reincarnation aside, however you might feel about that, this moment right here, you get one chance. When I’m looking back at it, I would love to be able to say that I did not alter any part of my life to cater to someone else’s opinion of what I should do or who I should be. And I would love to assist other people with obtaining the same, for lack of a better word, or lack of a better phrase, like a “no fucks given” mentality. ‘Cause I really don’t care, if you don’t like me, that’s fine, move on. If you’d love me, thank you. If you don’t think that the way that I’m living my life is conducive to success or conducive to happiness or you’re upset because I’m 31 and I’m not considering marriage or having children, that’s your things.
Jackie:
Those are your things. So, I feel like we need to just kind of let go of these stereotypes and societies telling us what we should and shouldn’t do and other people’s opinions dictating what we should and shouldn’t do and just live for ourselves and do what makes you happy. Because ultimately no matter what you have, you can have all the money in the world. You can have all the health in the world and being happy is the most important thing to me because you can have everything and still be sad.
Debbie:
There’s a lot of people out there with so much money but they’re still unhappy and most likely it’s because they’re not living for themselves. And you’re right, a lot of people are living for other people or they give too much energy into what other people are thinking about them instead of just doing what they really love to do. As long as it’s not hurting you or other people, you should do what you need to do.
Debbie:
Now, Jackie, are you working on anything currently that is really exciting to you?
Jackie:
I’m working on three projects right now but they all have very heavy nondisclosure agreements, so I’m not allowed to talk about those. But I can say that I am going to be really focusing more on Youtube for myself and I’m kind of growing myself into more of an activist kind of role, standing up for people and situations that I believe in. I feel that I have a platform and now it’s my turn to use it. I love to travel. I love to help people realize that you can travel affordably. But I feel like there’s also enough travel blogs out there giving that advice and I feel not purposeless, but I feel like a part of my purpose has been lost in Instagram and social media and things of that sort and I really am excited to move forward with more of a purpose in the next few months and hopefully by December or so, maybe even have a new website, a whole new brand in itself.
Debbie:
That sounds so exciting Jackie and I can’t wait to see what’s coming up for you. So, that’s going to be really exciting. For our listeners want to know more about you, where can they find you?
Jackie:
You can find me at Get Lost With Jackie on Instagram. You can find me at GetLostWithJackie.com on my website. I’m also Get Lost With Jackie on Youtube and Facebook and if you want to keep it personal and I’m just going to apologize in advance because this is where I am unapologetically myself. You can find me on Twitter. I’m @theblondenomad and that’s where I post memes. That’s where I am not politically correct. If you like Trump, do not find me there because you will not be happy with what I have to say. And that’s where I joke around. I curse there and I’m unapologetically myself there.
Debbie:
That sounds like where we should all look at. Thank you Jackie so much for being here today. I really appreciate you speaking with us.
Jackie:
Thank you so much for having me. I can’t wait to see also where you go. So this is very exciting, I think for both of us.
Listen to Jackie’s extended interview where she shares how to successfully monetize Instagram.
What you’ll find:
In this week’s extended interview Jackie shares how to effectively monetize Instagram. She gives tips on how to create successful content for brand collaborations, how to pitch to companies and so much more!
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