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Ep. 231: How this digital nomad thrives by traveling the world with Jackie Omotalade

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In this episode, I speak with Jackie who has been crisscrossing the world for over 25 years.

She is an O.G. digital nomad who lives by the motto: “if you ain’t thriving, you ain’t living right.”

She is a mother, serial entrepreneur, coach, and consultant who has lived in or visited over 70 countries.

Listen on to find out how this digital nomad coaches other women to live their best nomadic lifestyle.

Listen Below:

RELATED EPISODES:

Ep. 230: How this digital nomad explores the world as a travel journalist with James Clark
Ep. 229: 4 Year Anniversary Episode: Answering The Most Asked Questions From My Listeners
Ep. 228: How this travelling woman helps females move and work abroad with Jaime Kaplan-Perico

Transcription:

Debbie:

Hey everyone. Thank you so much for being here. I am really excited to be speaking with my guest today. I’m here with Jackie. 

Hey, Jackie, how are you? How are you?

Jackie:

Hey, Debbie. How are you?

Debbie:

I am wonderful. 

I love Jackie. We met today but her energy is already giving me life. So thank you, Jackie, for being here.

Jackie:

Well, thank you. Energy bounces off energy so that’s all you, girl. 

Debbie:

So, Jackie, can you tell us about you and why you live an offbeat life?

Jackie:

So my name is Jackie Omotalade and I consider myself, like, this OG digital nomad. And for me, my life is about living a life on my terms. Not that I’m not accountable to anyone because I got a little girl. I definitely have people that I am responsible for.

But I feel, like, it’s part of that responsibility. I need to be the best role model I can be for my daughter and doing that is living a life on my terms and I don’t necessarily know if it’s conventional. 

I know it’s not conventional in the sense that my dreams are not necessarily the “go to one place, live there for the rest of my life, and do that”. Like, I want to experience new things. I want to travel the world. I want to do all of that.

Debbie:

Love it. And that is something really special especially for a mother, for parents to do that because it is an example that you’re setting for your children and you have a really amazing mentality, you have this positive attitude. 

How did you get started on this path, Jackie? Because this is not, like you said, the norm, right? This is not what we’re taught to do. We’re taught to go to school, graduate, find a job, get married, have a house, have kids like But you took that to a different level. 

I mean, you’re still having a child, you still have your relationship but it’s in a different way that’s for you and what you want. 

Jackie:

So I will say for me, it started when I would say, like, an itty bitty. I’m unfortunate enough that I had a mother who really enjoyed travelling and always encouraged me, even when I was little, when I wasn’t silly traveling, just to books. 

I mean, when I was a kid, if there was a book reading competition, I would win it. I will coast the library and my mom always lets me check out the mats on all the books she bought me. I grew up pre-internet so she would find me every single, like, encyclopedia that I want, all that stuff. So I’m just looking up places and all that stuff. 

And when I was in high school, I actually decided that I was ready to go abroad. Like, Deuces. I’m from Pittsburgh, Pennsylvania. I just didn’t want to be there anymore. And I actually went to the library, my mom took me.

And I spent a week in the library, just researching programs: one, go abroad, study abroad, but two, have somebody pay for it. ‘Cause I didn’t come from a family who has money like that. If you had five grand, it’s in your bra for, like, a year. 

And so I wrote an application. I ended up getting accepted to a program and let me live in my senior year of high school in Germany. And after that, I got my little girl to pass so I could take my backpack and travel Europe.

Frankly, once that bug was in me, I knew I could do it because when you’re sixteen years old and get on a plane all by yourself and live with a family you don’t even know in a country you’ve never been to, at that point I had just picked Germany because it was a scholarship there. Like, I really didn’t know anything about Germany except World War II and that ain’t pretty. 

I definitely had a lot of stereotypes in my head about what it would be like to live in Germany but I was willing to see what it was like and go in with an open mind and I never regret it. I probably came back fifty pounds heavier because deserts in Germany are worth fighting for and my host mom was a pastry chef.

So we had this intimate relationship in terms of, like, that I was eating almost every day. And from there, it was just, like, “Okay, how can I make this happen?” Especially when you’re in a place where, like, you are bright. Where you can just hop on the train and you can be in a completely different country in an hour or 30 minutes, depending, right? 

It was just like, “Well, let me just hop here. Let me go to France.” And I ended up actually living in France for 8 months as well. Then I lived in Spain, “Let me just check Spain and just see what that life is like.”

I love meeting new people. I love even facing my own insecurities, my own prejudices because we all have unconscious biases, we all have stereotypes of what people are or are not. And just being forced to confront all that, deal with all that, being comfortable, being an independent woman.

It’s definitely hard when you take away everything that’s familiar to you. You can take away language. When you take away, like, a neighborhood, when you take away culture or history and what the norms are and just go for it and you are somewhat reliant on the assistance, the kindness of strangers.

And I will say that one thing that moving abroad has taught me is that human beings are of the essence despite all the stuff you hear in the news and the media. We’re good people.

Debbie:

Yeah.

And it’s really true, right? Because for the most part, everything that we hear in the news, media are what’s happening that’s bad. But for the most part, people are genuinely good. Just because we hear only the bad things, doesn’t mean everyone is like that. 

And that’s why traveling is such a huge part of really learning human nature and human beings and being connected with other people. Because unless we experience it personally, we cannot have a full understanding of what other cultures, other people are alike. And that’s, I think, one of the biggest ways to have a really full experience in life and have an open mind like that. 

And you are lucky enough to have a mom that encouraged that and I think we’re lucky when we have parents that really do that because unfortunately, that’s not everyone’s case. And I’m sure you’re giving that to your children as well, having that spirit of adventure, which is really important for everybody.

Love that you were able to do that, Jackie, at such a young age and fortunately you had that scholarship to travel. You went to school, you are supposed to have this job now, right? How did you go into the digital nomad lifestyle? How did you get into that process of working from anywhere?

Jackie:

So, just a couple of things: one, it was having a mindset of, “Yes. It is absolutely possible for me to live wherever I want, travel the world.” And I will say though it definitely was a process. Like, a couple of times I’ve been, throughout my life, an ex-pat. This means I had a job in, like, a different country because I think it’s definitely a leap when you are a person who was still conditioned. I mean, despite the fact that I think in many ways as a kid, I was very forward-thinking.

There’s still this condition society gives to you that you have to have, like, a job that gives you a salary every month, right?  And there are people who are location-dependent who have that. But at some point, I decided that it isn’t necessarily what I wanted for myself. Like, I love to work for myself. I love to create opportunities where I can make money. I went to law school so the idea that I would go from making six figures a year to you making $12,000 a year which is completely acceptable to live in many countries in the world, pretty well. 

For me, it just wasn’t an option for this type of lifestyle. I’m a fancy girl. I’m not going to lie. I like nice things and yes, I spent my twenties in youth hostels and backpacking. But now, me and my little girl, her name is Ruth, I got on a plane with her. 

I gave birth to her when I was in San Francisco and I got back on the plane with her when she was 10 days old and I got her and myself a first-class ticket and we were out again. I’m like, people got on the plane. And people got on the plane and one was like, “I’ve been flying my whole life and I’ve never flown first-class.  How old is she?” I was like, “She’s 10 days.”

And so for me, it’s very important that I create ways to generate wealth that, one, allows me to be whatever I want for the most part as long as I have a computer. For me, computers are very important. But then, two, in creating money, I wasn’t necessarily exchanging time for money. Like, most people get paid for working for 9-to-5 or per hour. I didn’t want that for myself. 

From 9 to 12, I want to be on the beach with my daughter and we are beach people. Like, we love the beach. That’s what I’m doing. That’s what I do. And so it was like, “All right. Let me think of a passive income, ways to make income.” But then, like, also let me think of the things that I’m really good at and, like, how can I turn those into money-making opportunities. 

So for me, it became getting super, super comfortable with numbers and with finances. And that’s not something most women are really, like, comfortable with. And it’s necessarily just budgeting because I’m not that girl who’s gonna wake up everyday and check my bank account how much money is there.

Like, I don’t want to worry about that. I’m not going to stress like that. Most of my bills are on. autopay anyway, I’ll check my account at the end of the month to make sure, like, nobody scammed me but I just did not. I want to understand my numbers but I don’t want to be watching my account like that and how can I get there. 

And then understanding real estate. I was lucky enough to have a cousin who is very, very much involved in, like, the real estate industry and how I can make real estate work for me. Once I just started, I was just going for things. I mean, especially with this digital age, there are so many different ways to make money online.

Some of them are, like, the silliest things in the world. Like, I have a friend and former client who makes money teaching people how to juggle. So, like, it can be something that you think, like, “That’s the dumbest skill set in the world.” 

And it’s so funny ‘cause I told my mom, “Oh, Mom, I have this client who juggles.” And my mom was like, “Oh, I want to take that course,” and I was like, “Who knew there’s a market for people who want to juggle?” Clearly, my mom’s in my client’s graphics. 

Debbie:

Yeah. I mean, it’s like even the most ridiculous things that you’re thinking of, like, you’re talking about right now, Jackie, like, juggling, people will want to do it, which is pretty incredible. That’s the beauty of the internet age now is that you can literally find a client for anything.

Jackie:

And what most people struggle with is finding like, “Who’s gonna try this.”  Like, it’s one thing to say there are people out there who want to, like, juggle and I don’t think it’s for everybody. And I think that’s one of the mistakes a lot of women make when they go and do business like, “Oh, my pipes are wonderful. I’m going to sell it to everybody.” Now, everybody doesn’t want what you got. And that’s okay.

Even in my consulting and coaching work, everybody ain’t my client and have those people That ain’t my people, I don’t want to be my people ’cause we wouldn’t have a good working relationship. And that’s when you get bad reviews and bad reviews do nothing for you, right? And it just makes your time miserable.

And again, as I separate myself and time from money, although I understand that relationship in some cases is very necessary especially when you’re doing coaching and consulting. If I’m going to exchange my time for money, I want to be in a working relationship where we’re both satisfied.

Debbie:

Yeah. And I definitely know where you’re coming from, Jackie, and I talked about this and in another episode, a lot of times we don’t realize that we also have the power in terms of the clients that we’re actually bringing into our program or bringing into our business, right? 

It’s really interesting because we do have that power and a lot of times we give too much power to other people. And then when you take a step back you’re like, “Yeah, I don’t need to bring in somebody that I don’t click with. Yes, the money is great but then I can find somebody who fits in better and I’m making money and I’m loving what I’m doing.”

But it does take a little bit of time to learn that especially if you’re just starting out and you’re trying to bring in as much money as you can bring in. That’s why, I don’t know, It’s like that scarcity mindset that we all have. And in the beginning, it’s definitely brutal and then you learn as you go. But I love that you’re able to do that, Jackie. And you have such a passion for what you do. 

I do want to talk about the things that you said about not exchanging time for money and you have all of these different streams of income. Can you tell us about some of them, how you found your way into them, and how you’re bringing money in all of these different ways? 

Jackie:

Oh, yeah. Let’s get in some numbers. Let’s talk about that stuff.

First of all, some of my main bread and butter. My background is in, like, technology, particularly disruptive technology policy. So when I say it, people are like, “Jackie, that’s a mouthful. What is disruptive technology policy?” 

Think of any technology that is truly, like, revolutionizing the world. So be it the sharing economy, fintech, which is financial technology, digital payments, all that stuff, right? Most of these companies have engineers who have these fabulous ideas and they’re like, “I built it. Now, I’m going to put it out in the world.” And governments are like, Hold up! I don’t know what that is. What are you doing? Where are you flying a drone?” All that stuff. 

So I am a person from a policy and regulatory perspective. I usually advise these technology companies on, “Okay. This is the opposition that you’re gonna meet, these are the government officials you need to talk to. This is some of the messaging that you need to have so that people, communities, government, regulators. understand what you’re bringing forth to the world.” 

Then also came some criticism of like, “Everybody ain’t okay with a drone flying over their house. Like, it could actually bear that buzzing noise looking in your window. It can be very annoying. Invasion of privacy.” So, like, “What facts should I do to mitigate against that?” So that’s one of the things that I do.

And so the next bucket is I also do a lot of consulting and coaching for women, mainly black women who you see on the six-figure, high six-figure income level who are interested in location-independence moving abroad or becoming a digital nomad. 

Because when you’ve been working 15 to 20 years, making a hundred, $200,000, the idea of just getting up and leaving your job and traveling, while exciting, there might have been a movie about it, it can be very scary when you’re like, “I got a house, I got bills. I got all these different things that I have to factor in and how can I make this happen?”

Most of the women are like, “Jackie, I ain’t 22. I’m not coming in hot. That’s not how I live.” And I always tell them, “It doesn’t matter though. You’re in a hot place.”

Debbie:

Even in Four Seasons, right? 

Jackie:

Even in Four Seasons, Mexico City. You’ll know.

I’ve been in what you’ll consider like high-income, high-net-worth neighborhood areas, and pretty much I’ve been with over 70 countries. And, like I said, I am not a budget traveller. I pay attention to money but I’m not a budget traveller.

Debbie:

Yeah. And it really comes down to your lifestyle. You talked about in your twenties when you were backpacking in, that’s the same way, like, with me, right? When we were younger, we didn’t have as much money so you’re traveling with the type of lifestyle that you have, and then once you get older and I’m like, “I’m in my thirties, I can’t be in a hostel anymore sharing bunk beds with people in their twenties. That’s just not how I’m going to travel.”

You can afford it more, you can go do something luxurious or middle ground. You don’t want to go that way but I’m like, “Yeah. I’ve been there, done that. Not going back there unless I have to,” but not looking down on it or anything.

Jackie:

Even if you were somebody in your thirties and forties and backpacking and stuff, that’s free. I mean, I like camping. I mean, I do enjoy camping but I can’t for a weekend. I can’t for a week, I can’t for 2 weeks. That’s not me.

And that’s okay. I always tell people, “You have to decide what makes you happy.” Even with me, like, location Independence. I have some clients who after we talked about it for a while they’re like, “Well, check it. I don’t necessarily know if I want to be somewhere every six weeks.” ‘Cause, that seems exotic at first but then the reality is, like, you’re moving every 6 weeks but even then,  6 to 9 months you start having a routine, you make friends, now I have a  daughter who I have to think about. She used to have a nanny who she’s very comfortable with.

And so I always say, at least with my lifestyle of slow traveling, sometimes it’s smarter. Like, sometimes I might stay in a place for a year. I mean, there’s also, like, those visas and all those other considerations as well but you really have to think for yourself, “What works for me.” 

Usually, I will stay in a region. When I was in Guatemala, I would explore all of Central and South America but I would still have a home in Guatemala that I’m renting and paying for so that my daughter has a sense of placement and this is where we come home to at the end going to Columbia or wherever we may be.

Debbie:

Yeah. And that’s really interesting because a lot of people who aren’t familiar with this type of lifestyle of being a digital nomad or a remote worker, think that we travel constantly, right? And, like you said, it really depends on your lifestyle. You can try it out, see how you’ll like it, and maybe it’s not the right thing for you.

For me personally, when I did that, like, I just couldn’t do the work that I needed to do. Like, there was too much distraction because if you’re only in a place for a certain amount of time and you’re like, “Oh my gosh, I have to work and then I have to see places. Like, I’m only here for two weeks. I can’t do all of this stuff.” 

And then I’m like, “I can’t do this.” Like, I would rather stay in one place and travel when I want to than I’m just, like, uprooting myself every few weeks. I know that wasn’t working for me and my husband has a job in New York City so, like, I can’t leave him for, like, a year and then just do that.

And there’s nothing wrong with any decision that is right for your lifestyle, and it changes too over time. We even mentioned it: when we were in our twenties, we backpacked, when we were in our thirties we’re like, “I’m flying first class and going to, like, the Four Seasons.”

think also, it’s because travel, the way you live, and the lifestyle that you have changes as you become older. You change as a person too. Your routine also changes. Now, Jackie, you have a daughter and it’s not just about you. So it’s a complete change but it’s still something that you love, which is incredible. 

Jackie:

It’s still something that I love. I appreciate it. I’m definitely more conscious about it. I’m definitely more conscious about my space, my time, and energy. Even something as simple as not being a parent versus being a parent, right?

Like, when I’m looking at AirBnBs or short-term rentals, like, a bathtub. A bathtub can actually be very difficult to find in some places in the world and my daughter loves her bath. She’s not really, like, a shower type. She’ll be 3 next month. So that’s kind of a bathtub age. 

But there’s just certain things, like, you pay attention to and then even as I grow in terms of my sense of, like, social justice and my responsibility to the world. 

In most of these countries, I’m hiring, like, nannies and like, “What is an equitable salary I would pay to a nanny? And how am I making sure that I’m not engaging in exploitative practices particularly as a black woman who’s come from a country where I definitely felt oppression? How am I making sure that I’m not going to Central and South America and because of the privilege that I have and the wealth that I bring that I’m not imposing those to indigenous people?”

And those are the things that I talk with my clients about. Those are all things I’m constantly just aware of and paying attention to. Even now, I’m not really traveling that much because of, like, covid. 

And one of the things that I always tell people is that most of the time, particularly this last two years with my daughter, I’ve been to countries with indigenous populations. So Central America, Mayan, etc… I’m like, “Diseases have wiped out these people.” So, as a person of privilege, most of my indigenous friends would never be able to leave their country of origin.

Like, never. Unless they use coyotes or whatever but they’re never getting a visa to go to Canada. Like, they’re just not. And so, like, what is my responsibility in that whole life ecosystem to keep them safe as well?

Debbie:

Yeah. Absolutely. And that’s something that a lot of people don’t usually take into consideration because for the most part, we just go there, we have a good time or, like, we’re meeting you people. And most of the time, you’re probably meeting ex-pats. 

And it’s so interesting to me when people go to a different country and they just want to meet people who are in similar backgrounds. I’m like, “This is kind of the whole point of traveling so you can learn about other cultures.” Like, even if you can’t really communicate with them and there’s a language barrier, it’s your responsibility to learn that, not there’s, right? Because you’re in that country. 

So I love when you mentioned that because there is a responsibility for us. We are definitely privileged in those terms and those terms where there are a lot more opportunities for us. We could leave our country. We could earn money the way we want to. Like, we could travel the way we want to whether it’s budget or luxury. 

So there’s so much to be really thankful for and I think that’s what I really love to share with people is just gratitude. Practicing gratitude with what we have. And I love that you’re sharing that as well, Jackie. And also you’re bringing that to your daughter as well and allowing her.

Because honestly for me when my husband and I have a kid, I’m like, “I want to explore other places, countries, and cultures with them. But then again, like you’re mentioning, it’s a really good education for her too. And you’re giving her so much of that. Love it. Love it, Jackie. 

Jackie:

Thank you!

Debbie:

Talking about all of these things that you’re doing. 

Let’s fast forward to about 30 to 40 years from now, Jackie, 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:

So I definitely want to be remembered for laughter. I definitely love to laugh and I think there’s definitely more of that in this world. But I also just want to be remembered for, like, my compassion, right? 

The more I travel, and I’ve been travelling while doing this for 25 years now, the more I realize, like, the interconnectedness of us all. And I don’t want to sound like a hippy-dippy wonky, you know that I did live in San Francisco for a while, right? 

Regardless of what your spiritual practices are, whether you believe in, like, a higher power or not, there is some energy that connects us all. And I want to do my part. Like, at the beginning of this call when you said, “I love your energy,” and I’m like, “Girl, energy bounces right out.”

So if you’re feeling that positive energy that’s ’cause you got the same. And I truly believe that it’s true, like, the core of my being.

And I would definitely want to be remembered as a person who brings laughter and light into this world to a degree. And I almost in some ways feel like my daughter is my legacy. Although I don’t necessarily put that burden on her shoulders. 

Like, I want her to be but she wants to be and what her destiny is. And I feel like my role as a parent is not necessary to force her into a category but to show her all the options that possibly exist and to support her in whatever direction she decides to choose. 

And then also just anybody who passes through my way in life. I feel like the greatest gift that you can give to someone else is just light and love. And again, not being a hippy-dippy wonky, but even on a practical level.

It’s funny because full circle, one of the young ladies that I work with, I met her at an event, probably like, fifteen years ago. Now she is in Mexico from South Africa. She’s not from South Africa, she’s living in South Africa. And I think she told me in one of our most recent sessions was that, ”I met you fifteen years ago at a party,” she said, “And I told you I wanted to go to the UK and get my Master’s Degree. And you said, ‘Of course, you do. And of course, you will.’”

And she said, “You were the only person who didn’t look at me like I was crazy. You didn’t say it was impossible. You didn’t say, “Girl, you got no money.” And I’m like, “You know me.” I believe in possibilities and I’ve seen possibilities in people. And I see them both on a physical and metaphysical level, right?

Like, you are infinite possibilities. And I say that to everyone like my clients, my daughter. Like, “The world is yours. You just have to decide where your place is. And if you figure out what your place is, you get there, and you change your mind, that’s okay too. Like, you can reinvent yourself 15 million different times. I know, I’ve done it in my life. 

Like, there are things that I’ve said, there’ve been opportunities that I’ve had where I said, “Guess what, this ain’t for me. I may be making a lot of money doing it but it’s not what’s filling my soul.

Debbie:

Yeah.

Jackie:

So I hope that in 30 or 40 years, I’m still, like, active and healthy but even if I’m not, I hope that the people that I’ve touched in my life, remember that as my legacy, that all things are definitely possible and truly the only limitations in our lives are ourselves, right?

And if you have the attitude that you can do it then you will do it. And that doesn’t mean that bad things don’t happen to you. It doesn’t mean that depression ain’t real. It. It doesn’t mean that you shouldn’t see a therapist, everybody should.

Sometimes you need help. Like, you need somebody to help you get through it. You may need a pill to get you there. I’m not advocating illegal drug use. You may need something, right? Every day is not going to be rainbows and sunflowers, although I really do like sunflowers. 

But, like, just know that at the end of the day, if you just keep moving forward, If you just keep showing up, if you put in the work, I’m not necessarily saying that work equals struggle because, yes, sometimes are a lot of times in our lives when we have to struggle but I don’t I honestly in the core of my being, think that we were put on this Earth to struggle.

Now, we put on the work but that doesn’t necessarily mean work is a bad thing. Like, there are some people living lives that are miserable. We were not put on this Earth to be miserable. So that means that it is upon you to figure out, like, what do you need to have in your life to make it a life that is worth living..

Debbie:

Yeah. And taking that accountability for yourself, right? Because there’s only so much that you can do to blame other people or be miserable. At some point, you have to take that into account. You can do it. You can definitely do it. 

I do want to go back to what you talked about, Jackie. About one of your clients saying that you’re the only one that believed in her, one of the only ones. And I think that’s one of the things that most people underestimate is having somebody actually believe in you, right? 

Because there are so many things that we want to do with our lives, and maybe you’re surrounded by a lot of naysayers because a lot of times people like this are from their own experiences, right? 

Maybe they tried to do something that they dreamed of, and that didn’t happen. And then once somebody else wants to go beyond what’s in their circle, it’s like, “You can’t do that because I couldn’t do it. So how can you do that?” 

And I love people, like, you Jackie, who are believers. Like, the Willy Wonkas of the world who, like, believe in the impossible even when everyone else doesn’t believe that. And I think those are the type of people that really make the world go round because you give others belief in themselves. 

And I think that’s very underestimated because it just takes one person to give you that uplift and you don’t know what this other person is capable of. They could have the capability to change the whole world if that was the case, maybe it could be. 

So, love that. Love what you’re doing and love this legacy. You’re already doing it. So you’re just going to keep going with it. I love it. 

Jackie:

I hope so. That’s my wish.

Debbie:

Love it.

So, Jackie before we say goodbye, I have five rapid questions for you. Are you ready?

Jackie:

I’m ready. Let’s do it, girl.

Debbie:

What would you say has been the best money you’ve ever spent while abroad and why?

Jackie:

The best money is always spent on a good meal. I mean, especially, street food. You see, the least amount of money you spend, the better the food is. I don’t know why that is but bring on the street food. Bring it on. And I have some diarrhea medicine with me but it was worth it. 

Debbie:

You and I are gonna be best friends. I feel the same way. I always say the weirdest, like, the ramshackle places have the better food. I’m like, “That’s why I don’t like fancy places ’cause they’re too expensive and the food is not even that good.” I’m like, “Bring me to the hole in the wall. That’s where you’ll find good food.”

Jackie:

I agree.

Debbie:

Can you describe your ideal day? What would it look like for you? 

Jackie:

My ideal day always starts, like, the same. I wake up around, like, five, six. Sometimes I get to rise to sunrise, sometimes I don’t, it doesn’t matter. I always do my meditation. I always do my positive affirmations. I always write in my journal. My day always has to begin that way. 

I’m a big outdoors person so depending on where I am in the world, what the weather’s like, I’m either at the beach for a minute, just for a minute, just to put my toes. Like, I’m a big ground person. So I feel like human beings at some point should touch the ground. 

I mean, I’m out there on the beach, touching the ground, doing my stretches. I’m not, like, a yoga person. Like, I’m not that girl but I would do some stretches. Some sort of physical movement that connects me with Earth and nature. I feel like I have to put myself in the balance.

And then it’s usually, like, I start my workday and start to do some emails and stuff. I’m very fortunate that I have a daughter who sleeps late.

Debbie:

Oh, nice.

Jackie:

She stays up late too but she’s two, she knows where she wants to be. I don’t really regulate her schedule.

So when my daughter wakes up, it is all about her. I’m a big advocate of world schooling. So most in her prime time is, like, the morning she’s the most pleasant. That’s when she’s  like, “Oh my God, Angel!” One it’s afternoon and it’s nap time, a little diva child comes out. No, just fatigue.

So you see I try to spend some time with her whatever work I need to do. ‘Cause when I think about my childhood, the time I get to spend with both my grandparents and, like, my parents as a child were stuff that I still remember. 

And it’s not like I planned. I mean, I see\ people on YouTube and Instagram, doing, like, all these elaborate things. Sometimes it’s watching YouTube and watching Blippi.

I don’t think Blippi’s strange but, like, my daughter is into him, so, like, whatever. Like, we’ll sit and watch him on YouTube. It could be collecting seashells or throwing rocks into the water. It doesn’t necessarily have to be, even when I say, like, world schooling, my daughter speaks Spanish. 

Sometimes it’s just going to the market together and letting her like, get a slice of, like, watermelon from, like, one of the local vendors. I mean there’s just a lot of different things that we just do, just hanging out together. Like, painting, building sandcastles. 

By the time she’ll come back, we’ll get something to eat, and then she’s ready for a nap. And then that’s why I should start hitting, like, working on whatever projects I have to do, whatever client I have to meet, meeting my web developer. Like, yeah, just one in the day.

That’s my typical day but it can vary depending on time zones.

Debbie:

I love it. I love that type of life that you’re building for yourself and your daughter because it’s definitely not the norm. And it’s okay not to live by everybody else’s standards and you created as you go and you learn. So definitely am a big believer in that as well, Jackie. 

So where would you say is the best place to live as a remote worker? 

Jackie:

For me, the best places are just anywhere with a wifi. I mean, I have to have a pretty strong wifi connection ‘cause I do a lot of, like, Zoom calls, I am managing a lot of different teams. I’m a big proponent of what you don’t necessarily enjoy doing – outsource but make sure you understand outsourcing.

I definitely don’t outsource any of my finance except my bookkeeping but I still meet with my bookkeeper every week. Girl, I want to know my numbers. I gotta know my money.

Debbie:

I love that. Yes.

It’s like you got to keep an eye on that. Yeah, that’s true. You gotta know what’s happening. It’s really important. Love that. 

So Jackie, if you could have a superpower, what would it be?

Jackie:

Probably it would be more time ‘cause that’s the only thing you really can’t get enough of

And I feel like the more I live, the more I want to live and the more I want to experience. So probably more time.

Debbie:

You can’t experience it all in a lifetime so if you could slow it down a little bit and also aging, that would be great.

Jackie:

I’m definitely feeling it.

Debbie:

Not even the way you look but, like, your body feels.

Jackie:

Yes. How quickly you recover from things. 

I mean, there were times where I remember I could stay up to 4 or 5 and get back up at 8 and be fine. And now, I’m like loaded at 10, latest.

Debbie:

Yeah. My goddaughter and her brother are the same age as your daughter. And I’m like, “How do they have so much energy? This should be the total opposite, when you’re young you shouldn’t have energy. As you get older, you get more and more ’cause now we’re using more energy. This is not right. This should not be like his but whatever.” 

So, what’s the one thing that you wish you would have done sooner?

Jackie:

I wish I would have trusted myself. I say that because I think there’s so many times I second-guessed myself and it took me six months to a year, 2 years, 10 years to decide to go for it. 

I mean, everything happens for a reason when it is supposed to happen but I think, “Man, if I have done that…” Even with real estate, I’m like, “If I had it when I graduated from law school if I really started investing in property, the way I’m doing this part of my life, I could’ve added three or four more zeros on all my bank accounts.”

So those are some of the things. I’m a big course person and a big coach person. So yes, I coach and I consult but I also have coaches that I consult. And I think that if you’re a good coach or consultant, you should have people. Like, I am always taking courses, and sometimes I’m like, “Man, I wish I had taken that course, like, 6 months ago.” “Cause there’s always you should learn.

And I’m always trying to become a better version of myself and how I live my life. But then also how I, like, run my business. I read one book a week, minimum. This year I’m trying to double it. So I’m trying to do two books a week. Sometimes just audiobooks and I used to be a book purist but I’m also a nomad so I can’t be home with all the books. 

Plus, I’m carrying a two-year-old who doesn’t want to walk most of the time and most of the time I don’t live in places that are stroller-friendly. So I’m just always just trying to learn and relearn and revisit different things.

And I think that is so important and I wish that I had trusted more of that in myself at a younger age.

Debbie:

Love that. And I think it always just happens as time passes. It’s like it takes a little bit of time to really learn that about yourself that you can trust your decisions, you can trust your instincts. But I’m glad that you were able to do that now. It’s, like, part of growing, I guess. 

Jackie:

It definitely is.

Debbie:

Well, thank you so much, Jackie, for being here with us. If our listeners want to know more about you, where can they find you? 

Jackie:

They can find me at TheJackieOLife.com. 

Debbie:

Perfect. Thank you so much, Jackie. We are so happy that you shared all of your insights with us today. We really appreciate you.

Jackie:

I appreciate you. Thank you so much for inviting me and thank you for this wonderful platform that you created for people looking for location independence.


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Show Credits:

Audio Engineer: Ben Smith

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