Ep. 296: How This Travel Expert Seizes Every Opportunity To See The World with Gabby Beckford
In this episode, I speak with Gabby who is a Solo Travel Expert and Opportunity Queen at packslight. She helps people seek risk, seize opportunity, and see the world!
Listen on to find out how this travel expert seizes every opportunity to see the world.
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Transcription:
Debbie:
Hey everyone. Thank you so much for being here. I am really excited to speak with my guest today. I’m here with Gabby.
Hi Gabby, how are you?
Gabby:
Hi, I’m doing great. How are you?
Debbie:
I’m wonderful. Thank you so much for taking your time to talk with us today about your lifestyle. Can you tell us more about you and why you live an offbeat life?
Gabby:
Yeah, so I would say offbeat is a great descriptor for my life. I’m a full-time digital nomad, which means that I work remotely from my laptop and my phone and travel full-time. I’m usually in a different country every month, if not more often than that. And that’s because I work for myself. My job is as a travel content creator and travel entrepreneur. And yeah, I kind of have made my own business in my, I DIY-ed my life in a very offbeat way. So, this is very fitting.
Debbie:
Yeah, and that’s why we love Gabby because she has so much to share and your journey is really interesting. Can you tell us how you actually got to becoming a digital nomad? Because I know for me growing up, this wasn’t even anything that I was like, oh, one day I hope to be a digital nomad and have a career in travel and be able to do this and also create an income from it. How did you get to this point where you can actually make this sustainable for yourself?
Gabby:
So I was the same way. I don’t think I heard the word digital nomad until I was in my twenties, if not my mid-twenties. So I knew though, from a young age, I remember actually this specific example. I was in my junior or senior year of high school and our teacher had us write down like letters to our future selves in like 10 years. And I wrote in my letter, I said, “I hope that you’re traveling the world. I hope you’re smoking hot and I hope you’re, you have financial freedom and you’re living and doing whatever you want to do.”. So I mean, hopefully I’ve hit all those, those milestones now. But I’ve always known that I wanted financial freedom and I’ve always known that no matter what my job looks like, I wanted that freedom to include the ability to travel. So, I got my degree in statistics, I worked as an engineer, kind of that first generation story.
But all the while in the background I was like, “How can I live the lifestyle I want to live? Like how can I wake up every morning loving my life?”, and that was trying to find a way to travel. So, I’ve always had kind of a hobby platform. I talked about travel sometimes inconsistently, for fun. And when I started my engineering job, I really just went crazy trying to like YouTube and ask questions and figure out ways that I could turn it into a somewhat sustainable business. And that’s how I became a digital nomad, is I went crazy on my side hustle and turned it into my main hustle and found a way to do it without needing an office and just wifi.
Debbie:
Yeah and you know, you mentioned having this traditional life being an engineer and pretty much doing what your parents are probably super proud of. Like, “Yay, she graduated. Now she has this engineering degree.”. How did you, I mean, obviously transitioning for you to, to being a content creator was a dream come true, but what about like your family? How did they take that? Were they surprised were they not? How did that go?
Gabby:
Yeah, I remember being absolutely terrified to tell my Dad that I wanted to quit my engineering job because I had a job with a company that was the same industry as him and I know that he kind of saw, like me following in his footsteps type stuff like that typical immigrant parent pressure of like, “Ah, okay, you’re making it like perfect all by design.”. Like, we’re just like little puzzle pieces in their bigger puzzle of success, you’re in the US and I remember being like, “Dang, I’m about to burn that to the ground. That’s so awkward.”. So I avoided telling my dad for a long time. I knew my mom would be supportive cause that’s just who she is, but I knew my dad would have a lot more, like, he would need a lot more time to come to terms with it. So, I tried to tell, I remember telling myself, “Okay, tell him earlier rather than later so you can, like, he can go through the grieving process while you still have your engineering job and then by the time you quit, he’ll be over it.”.
So, I told him like, my plan was always February 2020, which now in hindsight was like such an interesting timing to be planning to do that.
Debbie:
Yeah.
Gabby:
Yeah. And that plays into it too. But I was like, “Okay, February, 2020.”. So, I think maybe almost a year or a little bit less than a year before that. I told my dad right before the summer came and he went through every phase of grief, like, “I can’t believe it.”, like bargaining and like begging and like, “Please, you don’t know what it means to to be, you know, just coming here and like establishing yourself.”, and then like all that type of stuff. So, by the time I quit, he kind of was at that acceptance point and he was like, “You know what? If you can do it, you can do it. Like we’ll see what happens.”, and now he brags about me more than anybody.
Debbie:
Awww…
Gabby:
Like it’s the complete, the switch up. I’m like, “Remember when?”, He’s like, “Agagaga… No! and he’s like, “My daughter like, you have to see what Gabby’s doing, she’s in South Africa right now.”. He’s like my biggest fan. So, I’m like, I’m so glad I listened to myself cause like he, and he had to trust the process. He had to trust the process.
Debbie:
Oh my gosh, I love that because I think a lot of people who want to dive deep into this and do have those parents that are immigrants and my parents were immigrants, I’m an immigrant and that’s a really hard topic to broach because they work so hard and it’s not easy and when they finally see you do something that they can be proud of because of the hard work they’ve done that they feel like it’s part of their success as well. And you’re right, it’s such a hard thing to do, but you know what, it’s hard for them in the beginning as it is for us. But like you had mentioned Gabby, once you do it, you know, once you start doing things and you actually go for it and they see things happening, they become prouder than you and with what you’ve done with your life. So yeah, it is really tough to broach that subject. But if you work really hard and you’re as successful or more successful than you were with the previous career that you had, they’re going to be as happy, you know, that you’ve done it. And like you said, your dad is your biggest fan now.
Gabby:
That’s exactly it, like setting us up for success here in the US and like doing, making the sacrifices he made, that was what he knew best, but like now this is what I know best and so now he has to trust the process with me and it’s definitely paid off. So, if you’re listening to this, yeah, trust your process. You got it.
Debbie:
And I say this all the time too. I say that, you know, my parents work so hard for us to get to the United States that I don’t want to do something that I’m just okay with, just to have an okay life, like they worked so hard, like why not have the best life you can possibly have with everything that is in our fingertips? Because being here in the United States, you do have a lot of opportunities. So, if you can’t have these opportunities where you were, why not take advantage of that now? So, I think, and I tell my, I, you know, I tell my parents that I’m like, you know, I am doing things that we never could have done there. So you should be prouder actually.
Gabby:
That’s exactly it. That’s exactly it. You’re so right.
Debbie:
I love that. So as a digital nomad because you travel quite often, you mentioned you travel every single month, that is amazing because I tried that and it was exhausting for me. How is that like for you, Gabby, because that’s, I’m like, I wish I could do that because that would be fantastic to see so many different places.
Gabby:
You know, on paper, I think it’s so interesting that I pursued this lifestyle and that I really love it because on paper I am actually an introvert as opposite to my social media as that seems. I love my alone time. I like a routine. I love my comfy bed. But as much as I love those things, like I, it just doesn’t outweigh the fact that I love learning more than that. I love being in a new environment. I love changes around me. I love, like, I honestly feel like the more I learn about the world and the more I experience the world, the more I learn about myself, which is what every person does just by living. So like I feel like I get to live life on steroids like four times, like expert mode by traveling so much and I learn so much more about myself and the world around me by doing it.
Debbie:
Yeah. And that’s the thing about life. I feel like for me, like when I see people live lives like you, Gabby, I’m like, they’re literally living so many different lives. Like you were an engineer, now you’re a content creator, you’re a digital nomad. Like I think that’s how life should be. You should have different lives, right? By the time we’re like in our eighties, we should have had like 50 or more lives that we conquered and saw. And I think that’s what really living is. And you’re definitely doing that.
Gabby:
That’s exactly it. I always have felt like, “Okay, we live in the US like, there’s the expectation, you know, you hit a certain age and like you, like your brain flips into this other mode and you’re like, I want stability, I want investments and land and like a family and stuff.”. And I’m like, “I know I’ll probably get there one day, but like while I have this urge to see the world, I’m definitely gonna try to do it as much as I possibly can because that stuff will be waiting.”. It will be there. I will not miss out on it. But this like being this young and being able to like just wake up and buy a flight to somewhere else, a different city and yeah, I’ve tried to make it the most of it while I have it.
Debbie:
Yeah. And why not you can do it. Why not?
Gabby:
Exactly. It’s such a huge privilege and it’s such an amazing life to live. I’m so grateful and that’s why I started my platform really is cause I saw just a little small pathway to be able to do that and I just kind of kept digging at it and found my own way. And now I wanna help other people be able to do that for themselves.
Debbie:
And you know, you make it look so easy because you definitely have social media and your website, it’s just so beautiful. You’re in different locations. But don’t get me wrong, or Gabby, like, it’s a lot of hard work. Now, Gabby, I know you worked your butt off to get to where you are and I’m sure you worked harder than you getting into engineering. So can you tell us your process of actually, because you know, we see it all the time, there’s a lot of people that wanna get to where you are, but not many people get to do it. Not many people get to make this actually sustainable, actually something that becomes a career they can make money from that they can actually live off of. How did this process go for you? Because I know like, just seeing you, we can easily say, “Well, Gabby just did it and then it happened.”, but what’s like the middle part, you know, that got you there?
Gabby:
No, a hundred percent. I know exactly what you mean. That middle part is what I’m always trying to like dig out of other people I find inspiration from like, “You woke up and you were born and then you were just like successful?, like, “What happened in between that?”.
Debbie:
Yeah.
Gabby:
And for me, I think the part that goes unseen is the failures, like I try to share the not, I mean as probably as many failures, like there’s a, if I shared the accurately how many times I’ve failed compared to how many times I’ve succeeded, people would look at myself and be like, “Ugh, I feel so bad for her, like Jesus Christ, like, ugh, don’t you have any shame? Like, that’s so embarrassing.”, because that’s how many times I’ve failed on this path for as much success I’ve had, if you imagine that as a loaf of bread, the amount of failures I’ve had is like a triple decker wedding cake.
Debbie:
Oh my gosh.
Gabby:
Like, in comparison, but that’s just what people don’t see because I fail at 4:00 AM in the morning when I like try to publish a blog post and it doesn’t go like technology messes up and it all gets deleted and I have to start from scratch.
Or I fail when I apply for a grant that I’ve applied to three years in a row for the third time and I still get rejected. But that organization now knows my name and they DM me on the side and say, “Okay, you’re really, like, stop applying for this, you’re so bad for it, but you know what you are good for this one, like, apply to this instead.”, and like, those are the moments that lead to my success and have built my success. Like I have built my success on a bed of horrific failures, but the thing that makes me different than I think the rest, like than a lot of people that don’t make it to this point is that I accept failure as part of the process. I welcome it because failure means that I know what not to do next time. And failure means that, “Okay, I didn’t get it, but people know my name in that room now.”, and I’m able to, like I said, use those failures as cute little stepping stones to where I want to go instead of looking at them as like reflections of myself or like signs that I should stop. I’m like, “All right, throw it on the pile. I’m about to step on it. Let’s keep going.”.
Debbie:
And you know what I think it’s really interesting and I’ve interviewed hundreds of people and pretty much one common denominator for everyone that I’ve interviewed and is successful at what they do is they talk about that it’s like taking failure and not seeing it as that, right? And kind of reevaluating our mindset when we think about it because there’s a lot of shame to the word failure and experiencing failure. And I think for, for somebody like you, Gabby, you see it as a learning experience instead of something that’s going to stop you. You see it as something that’s actually going to allow you to see what you can become better at instead of something that you should be ashamed of. And you know, we, we see that all the time too. Like we see it on social media, people will share their failure and then it becomes this like heroic story, right?
Gabby:
Mm-hmm.
Debbie:
Once they overcome that and I think that could be a part of everyone’s heroic story. It’s like, “Tell us how you failed and tell us where it got you.”, because there’s just so many things, so many incredible things that happens from that. And I love that you say you failed so many times and it’s embarrassing sometimes, but it got you to where you are. And I think it’s also just persistence. Like you just not giving up. Even though, sometimes you’re just like, “What the heck am I doing with my life?”, you know? Because like I question myself everyday, every time like everyday there’s actually a failure that happens and you’re like, “What is happening? What am I doing? Wha- I don’t know why I’m still doing this.”.
Gabby:
Yeah, yeah. And I will say, like hearing you talk about that, I think a huge element of the persistence and the perspective on failure, whether we acknowledge it or not, as creators and entrepreneurs, is the support system you have. And yeah, I don’t wanna assume that everyone has that at home or like that that’s like a given because it’s often not. But curating that support system on your social media, like in your online life, in your friendship life, in the relationships that you surround yourself with is so important, because when you get that 4:00 AM failure and you tell your best friend or you tell anyone, that person, their validation of you could just be what it takes to keep going forward. So, I think having, I mean, I don’t know how that kind of spins into having really strong boundaries and like knowing what you want for yourself and all that type of stuff that’s like, you’re the sum of the five people you surround yourself with.
Like, making sure you’re creating an environment of support around yourself and like ambition and just moving forward is going to help you be able to get back up when you’re knocked down, because if you have like naysayers or haters or like non-supportive people around you and they keep reinforcing those, your own negative thoughts, it can keep you down for sure. So, I think that’s one thing is, not that my Dad was a hater, but my dad was like a questioner, you know, my Dad had questions and so I definitely had to lean on my Mom more and sometimes or on my friends and be like, “Okay, am I crazy?”, and I took those friends who were like, “You have to bet on you, like I see your potential girl, like keep going.”. They actually were probably what kept me from closing my laptop at 4:00 AM, so making that environment positive.
Debbie:
Yeah, I completely agree with that. And you know, the, and this is the thing, I’ve thought about this actually, Gabby, for, for a long time because my parents, well both of my parents are like your Dad. They’re both like naysayers, And I thought about this and especially I completely agree with like just surrounding yourself with people that lift you up and not to say like they’re just gonna be yes people to you cause I don’t like that either. I would rather have people who are honest and tell me the truth then tell me just everything is doing great and you know, all of a sudden it’s not, and you know, it’s just fake. Like, I would rather have the reality than that, but I do have to say that I love when people tell you things without ego, you know what I mean?
Like, they truly want what’s best for you. They can be honest with you, they can be supportive because I have found, I don’t know if you’ve ever experienced this too, Gabby, like there’s people that will tell you things and it’s not because they want what’s best for you, it’s because maybe they’re insecure,
Gabby:
Mm-hmm.
Debbie:
or maybe they haven’t done it and they will tell you it can’t be done and then you begin to question yourself and not in a good way. So yeah, protecting yourself and your energy is so important. And I also like, when I first began creating content, like I thought, “Oh I can’t, you know, like, there’s just certain friends that don’t understand it, so I shouldn’t talk to them.”, and I find that now as I’ve done this for like over five years now, I’m like, “I kind of like having friends too that are not content creators,”, because sometimes I don’t want to be in that space all the time and talk about like work and having my thoughts and different things because it can be overwhelming too. So, it’s so important having that mental like balance with yourself too and really finding the right people and you know, I don’t, you know, you mentioned too, Gabby, that you’re an introvert and I’m like, I’ve become an introvert since covid and I’m like, I just have a small amount of people in my group now and I am really loving it.
Gabby:
Yeah, exactly, you get to like be so intentional about where you share your energy and also what energy you accept, but I totally agree with you too, that it’s healthy to have people who don’t agree with you all the time and it’s healthy to have people who are not in your same circle, like you said, “Yes Men” or like “Fans” or like, you just have to have people who will look at what you’re doing and be like, “Babe, that’s dumb.”, like, “Look at me babe, no, don’t do that.”.
Debbie:
Yeah.
Gabby:
And you’re like, “What?”, and like you take a step back and you’re like, “I’m so glad someone told me, like no one told me like, what the heck?”, Like yeah, I think the people who care about you are are not always going to agree with you or like support you 100%, but they will always like trust that you know best in your business and like they’ll be like, “I think you’re gonna fail, but even if you do fail, I know that you’re gonna spin that around too. So like you do, you babe.”, and I’m like, “Okay, good, let me fail. Like let me do that.”, like I know those are my best friends.
Debbie:
Yeah, yeah, yeah, having people to really have your back really, truly have your back and you can argue with them about things and you’re still friends, like you can argue with somebody respectfully, and I think that’s, I don’t know, I feel like that’s so rare now, especially with all the climate, like I feel like it’s so rare to, to speak your mind, to argue with somebody but still respect each other and actually listen. And I feel like especially now, that’s such an important thing to have in our lives, you know, like trusting somebody like that with your opinion and being really truly yourself and being comfortable and having that is, is a real blessing to tell you the truth.
Gabby:
I totally agree, it makes you feel like you’re not crazy because you can feel like you have a great idea and if everyone says yes, even you will start to be like, “That’s suspicious.”. No, like, everyone thinks it’s perfect? Like there’s no, like, that’s not healthy either. So, it makes you feel sane to have a healthy amount of contrast and a healthy amount of like, questions and you know, analysis to what you’re doing and why you’re doing it. It really is like the perfect balance.
Debbie:
Yeah, absolutely. So I don’t know, I think as we become older too, it becomes so much more valuable, the people that really surround us for the right reasons and really there for us. So, Gabby, going back to what you had mentioned before, you thought that February, 2020 was gonna be the time that you would quit everything. So, going back to that, cause that was an interesting date and you didn’t know what was gonna happen before, did you stick to that plan? Did you leave your job in February, 2020? And how did that go? Because you’re in the travel agency and I know that was a crazy time for everybody.
Gabby:
Yes. Yeah, I had planned, like, I started my engineering job in June, 2018 and I had thought, “Okay, for me it’s going to be like spring 2020, that’s when I’m going to quit this job. And like, we’ll see where I’m at then if my business is moving, like what am I going to do next, like that’s what I’m going to re-analyze.”. And so that came and it was February 2020 and actually it was Valentine’s Day, so it was a Friday the 14th 2020, February. And I was like, “All right, this is it.”, and I put in my two weeks notice and I like, I had put in my two weeks notice in the beginning of February, so I turned in my badge on the 14th and like I left work that day on that Friday, crying in my car cause my engineering job was really nice, like the company was fantastic and like the money was great and I was like the youngest on my team by like 15 years and it was a really great place to be, there was no reason to leave other than that I knew it was a small pot for me who wanted to be a big tree one day.
So, like, it was just cute, but I knew I couldn’t stay there if I wanted to grow and do what I wanted to do. So I left. Fantastic. I think literally five days later I started hearing whispers of like ‘pandemic’, like, “What? Something’s happening, like what is corona? Like, Corona.”, and a week after that, the first week of March, things started shutting down and I had a one-way flight to Bali booked and I had to decide if I was going to get on that flight or stay with my family in my family’s house. And I ultimately, I was like, “Should I be trapped in Bali or trapped in Virginia?”, and I was like, “Uh, duh, Bali.”. But I ultimately decided to stay with my family, like, you know, just in case, we didn’t know really anything at that time about the virus and I was like, I think if something happened I’d want to be in the US Like, so instead of my year of travel, like I planned, I had a year of lockdown, which was in itself a blessing in disguise, kind of, not really in disguise, but it was a silver lining, that actually was beneficial for my business in the long run.
Debbie:
So what did you do during that year of lockdown? Like how did you prepare for all of this? Because you still left, you were still really, you know, gungho about pursuing this. What did you do in that time to really prepare once things started to open up?
Gabby:
Yeah, I think the best thing I did in that spring 2020 period was not plan. That’s probably the strongest thing I did because I quit my job with the expectation that I would fly to Bali and like use what a little savings I had to just kind of coast and figure the next step out. While I was there, I didn’t have a plan. My plan was like, be flexible and like see what comes. So, Global Pandemic, I’m like, “Okay, I didn’t roll bad dice.”, like who could have prepared for that? But, no one could have. So, the whole travel industry and actually every industry was put to immediate stop and I just, in my mind I knew that all these big companies and all the magazines and stuff, all of their marketing plans for 2020 to, well, 2020 were like thrown out of the window.
So, I could see that it was a blank slate for everybody in like every industry cause, yeah, what? Like, you’re going to talk about the five best ways to travel this summer in a pandemic? No, like you’re, all that’s in the trash now. So, I saw that as an opportunity space and the first thing I did was start pitching absolutely everybody. And I think I kept it short and sweet and I was just, I sent like maybe 20 emails a day and I was like, “Hey, I know your marketing plan’s on fire, but I would love to talk for Lonely Planet about waste that you can keep your travel, your love of travel alive while at home or like ways that you can relive your old trips to like keep your love of travel alive.”, and I did that for, I sent so many of those pitches out and you know, of a hundred pitches, maybe 10 people got back, but those 10 got me landed in the New York Times in Good Morning America and Lonely Planet and I won an award and like those were just enough for me to start building momentum for my, my platform that perseverance, man!
Debbie:
Yeah, and you took advantage of that. Like instead of being down and out and was like, “Okay, how can I get my old job back? Because this is not how I thought it was gonna be.”, you were like, “All right, well there’s opportunities here that I could take advantage of.”, and that’s exactly what you did. I love that.
Gabby:
I literally was like looking at my phone for maybe two hours that first day of lockdown and I was like, “Should I call my boss? Like if I called, would he answer?”, and I was like, literally, you could see the devil on each shoulder and like my phone struggling not to like press the dial button, they’re like, no, cause I was 24 at this time too. So, I’m like, “If I was ever gonna quit my job, it has to be now.”, if I had just waited one week to quit my job and you know, if I had heard about the pandemic, I probably wouldn’t have been as confident in doing it and I probably would’ve stayed that job and who knows if I’d ever have would’ve gotten here. So, it was divine timing, but I looked at that phone, I was like, it was on the screen to dial, but I didn’t do it.
Debbie:
Well, and that’s the thing, it’s you’re taking a risk on yourself. You’re taking a risk on the dream. Like it’s all a risk if you want to do something like this. And you know what, it could have gone either way, but hey, you took a risk on yourself and here we are right now living your, your digital nomad dream life.
Gabby:
Exactly. And I think about that all the time. Like my first thought is, “Okay, what if I had made that call and been stuck at my job?”, like “What if I had gone back to that?”, but I actually know that no matter if I had done that, I’m sure I would’ve quit like three months later anyway. Like I, this, all paths were bringing me here and you know, if I think about like, “Oh, what if I had done this, maybe I’d be further ahead.”, “Okay, what if I had done that and I’d been further behind?”, like, it really doesn’t help you to think about the what ifs, but I just have to believe that what I’m doing now is so impactful and so powerful for me and my community that like all the roads would’ve dumped me off here somehow. Like, I could have gone to Hollywood, been an actress and I’m sure I would’ve ended up here anyway because this is where I’m meant to be. So, I’m good with that.
Debbie:
Yeah, I love that. And it’s where it led you and also you work super hard for it, you know?
Gabby:
Yeah.
Debbie:
It’s just a matter of time and it’s inevitable that you are going to be here, but I love that. So, Gabby, let’s look forward to maybe 40 to 50 years from now and you’re looking back at your life, what legacy would you like to leave and what do you wanna be remembered for?
Gabby:
All right, so I’m 75. Hopefully, I’m just one of those hot grandmas on TikTok who just like has an amazing wardrobe and is like, “I’m never going to dress boring. Why would I do that?”, so, I hope that’s who I am at 75 and I’m hoping that my legacy is like changing the structural foundation of the way people think about themselves and the way they think about travel as an impact on their lives. Like, I’m hoping I leave a legacy that makes travel more accessible for more marginalized groups. I’m hoping I leave a legacy of like helping the world and not hurting it through travel. Like, hopefully the technology and, you know, society catches up that travel can be sustainable and enjoyable, like fun and not hurt the earth. And I’m hoping that people remember me and like think of me and be like, “Okay, Gabby could do it, I can do it.”, like, I’m hoping that’s just the immediate, like they think of Dr. Seuss and they’re like, “Okay, that guy rhymed.”, they think of me, they think of Gabby Beckford, and they’re like, “Okay, that’s the underdog story of the century. Like, we can do it.”.
Debbie:
Yeah. And you know, that’s a part of that and a biggest part of that is you actually doing it yourself because it’s one thing to think about it, it’s another thing to actually see somebody accomplish that. And you’re a huge part of, of being able to do that and people seeing it. So, you’re definitely on your way there, Gabby, if not, you know, you’re a huge part of that already. So, your story is so incredible and we love hearing it. If our listeners wanna learn more about you, where can they find you?
Gabby:
Yes, if you type in packslight.com, you’ll be led to my website, and from there, like all roads to heaven, start at packslight.com. I have my social media there, I have my courses there and I have my blog posts and all my little trinkets there, so, packslight.com.
Listen to Gabby’s extended interview as she talks about how delusional confidence can lead to self empowerment.
What you’ll find:
In this extended interview, travel expert, Gabby Beckford, talks to us about delusional confidence and how it can lead to self empowerment.
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