Digital Nomad Life After 50 with Jannette Anderson

Is retirement the finish line or your most creative chapter? Senior digital nomad Jannette Anderson reveals how to turn your wisdom into wealth and freedom after 50. Stop being "invisible" and start your boldest act yet. [See More]

What if retirement isn’t the finish line, but the start of your most creative chapter? In this episode, we sit down with business expansionist and senior digital nomad Jannette Anderson to explore how mature professionals can reclaim their autonomy. If you’ve felt the sting of ageism in the workplace or feel "unemployable" because of your vast experience, Jeanette proves that your wisdom is actually your greatest asset for building a laptop lifestyle over 50.

We dive deep into:

• Overcoming Ageism: How to flip the script when you feel invisible and own your value in rooms where deals get made.
• The "Maturepreneur" Reality: What it actually looks like to downsize dramatically and build a steady remote income across global time zones.
• Wisdom to Wealth: Moving from the corporate trenches to a digital platform that solves real-world problems.
• Combatting Self-Talk: Breaking the internal limiting beliefs about age, technology, and starting "too late."

The "Clarity Compass" Framework: Jannette unpacks her practical three-part framework for a bold "Second Act":

1. Clarify: Define the vision for the next third of your life.
2. Connect: Link your past lessons to a deeper future purpose.
3. Craft: Create a monetization plan that fits your energy, skills, and market demand.

For a similar episode on living a digital nomadic life over 50 check out episode 139 of Aging With Purpose and Passion and if you know others who would benefit from this episode, please drop a review and share it with a friend

Resources: For more podcasts for women over 50, Older Women and Friends hosted by Award-winning author Jane Leder and guests take a deep dive into the joys and challenges of being an older woman. https://janeleder.net/podcast/

Jannette Anderson – Founder, Maturepreneur World

jannette@bodacity.ca
🌐 https://maturepreneur.world
📸 https://www.instagram.com/maturepreneurworld
💼 https://www.linkedin.com/in/jannetteanderson

Beverley Glazer, MA, ICF – Reinvention and Empowerment Coach for women 50+

📧 Bev@reinventImpossible.com
🌐 https://reinventImpossible.com
💼 https://www.linkedin.com/in/beverleyglazer
📘 https://www.facebook.com/reinventImpossible
👥 https://www.facebook.com/groups/womenover50rock
📸 https://www.instagram.com/beverleyglazer_reinvention/

🎁 BONUS: Tired of 3 AM Overthinking? Get the "Stuck to Unstoppable" Roadmap and receive my weekly strategic insights for women 50+ delivered to your inbox every weekend. GET THE FREE RESOURCE Here: https://reinvent-impossible.aweb.page/from-stuck-to-unstoppable

Have feedback or a powerful story that's worth telling? Contact us at info@Reinventimpossible.com

Chapters

• 0:07 Welcome And Episode Setup
• 0:33 Is Retirement The Beginning?
• 0:52 Meet Jeanette Anderson
• 1:37 First Venture At Age Five
• 4:20 Corporate Trenches And “Unemployable”
• 8:31 Digital Nomad Life And Letting Go
• 11:48 Confronting Ageism In Entrepreneurship
• 14:22 Mindset Shifts For Midlife Earners
• 17:39 Vision, Purpose, Monetization Framework
• 21:05 Key Takeaways And Next Steps
• 22:58 Links, Free Guide, And Closing

Transcript

Announcer: 0:07

Welcome to Aging with Purpose and Passion, the podcast designed to inspire your greatness and thrive through life. Get ready to conquer your fears. Here's your host, psychotherapist, coach, and empowerment expert, Beverley Glazer.

Beverley Glazer: 0:33

What if retirement was just the beginning? Welcome to Aging with Purpose and Passion. I'm Beverley Glazer, a transition coach and catalyst for women who are ready to raise the bar in their own lives. And you can find me on reinventimpossible.com. Jannette Anderson is a business expansionist, a digital nomad, and the fiery founder of Maturepreneur World. After realizing that she was unemployable, Jannette sold her house, hit the road, and built a life and a movement that proves age is not a limitation. If you've ever felt overlooked and underestimated or ready to increase your income, this conversation is exactly what you need. Welcome, Jeanette. Hi, Beverley. I'm so happy to see you again. Yes, happy to see you too. And let me ask you, were you always an entrepreneur?

Jannette Anderson: 1:37

I pretty sure I came out of the womb with the briefcase in hand, Beverley. I'm I'm 90% sure. I uh I have my very first business when I was four or almost five. Um my I wanted the book Heidi. I learned how to read early because I grew up with lots of chaos and drama and trauma and stuff. And so books were my reference. And we I I begged my mom and begged and begged and begged and begged. And finally she turned around one day and yelled, No, we can't afford it. And I was so shocked, not by what she said, because I heard that all the time, but by the look on her face. She was, it was sadness and despair and frustration, and and just that kind of defeated look that I did, even though it was five, I decided I never wanted to see that look on someone's face again. And and that became the beginning of why I do what I do. But you know, kids, we don't overcomplicate things. Uh, it's like no money, get money, right? Adults would make it really complicated, but kids, ah, solution, get money. So I decided I was gonna have a business. I had seen some neighbors have a garage sale. So one day when mama was at work, someone was probably supposed to be watching me, but I don't know, back in 1965, it was a little more lax. Um, and so I hauled everything I could out of the house. I priced it because literally I could count money before I could read. And and um and I sold it. I was so excited. I made $13.72. I remember to this day, Beverley. I can't remember what I had for lunch yesterday, but I remember that. And I was happy because, you know, problem solution, right? Now we can get the book. But just surprisingly, my mom didn't see it that way when she got home. She was very unhappy. I sold a lot of our household knickknacks and Ivy Dumpsons, and her favorite pink wool dress, which was brand new and still had the price tag on it. Um no. So I got spanked. She took my money. I had to go back and buy back everything I could. The kids wouldn't sell me back my toys, so I lost most of my toys. Uh, so many people would say it wasn't a very good, successful first business venture, but I learned two really important lessons. Uh, one, don't go into business with family. I'm kind of kidding, but not really. Uh, two is that we can take our destiny into our own hands with business. We can make dreams come true. We can have what we want when we take the effort, make the effort, and create those solutions that serve us and other people. So, yes, I would say that's a long-winded answer to your question. I've always been entrepreneurial, and that was my very first venture.

Beverley Glazer: 4:20

Right. But you didn't go right into business. You were in corporate for a while.

Jannette Anderson: 4:24

Well, I was actually in business quite a bit growing up. Like, I mean, I I always had a side hustle. I had jobs, like I waitressed and stuff from a very early age. Um, and I did go into corporate, but but I I say I've done my time in the corporate trenches. I've kind of about every seven years, I go back into corporate because I go, ooh, benefits and stability and security in theory. Oh my. And then I go back in and I'm there about two maximum two and a half years, and I go, ooh, bureaucracy and BS and politics, oh my. And then I leave and go back and start my business again. So I've done that uh now I've uh three times. So I've had four iterations of my business, uh, but I was permanently cured in 2001. I don't think I'll ever go back into corporate except perhaps to consult, and even that's with some trepidation. Um uh so yeah, I've always been entrepreneurial. And yes, I've done my time in the corporate tensions, doing everything from running a print shop press to being VP of professional services for a Fortune 500 company.

Beverley Glazer: 5:30

Whoa. And you also came up with telling me that you are unemployable. And I understand exactly what that means, because I've heard CEOs saying I am unemployable, and quite frankly, I am unemployable too. But what do you mean by that?

Jannette Anderson: 5:47

Well, I tend to be a visionary, as many entrepreneurs are. Uh, visionaries often don't do well in organizations because uh it's supposed to be the organization that has the vision, not you. And so sometimes you can pull in different directions. Uh, I tend to be pretty pragmatic about getting stuff done. I've been entrepreneur almost my life, so it's very action-oriented, not process-oriented or processed, depending on where you're from. Um, and so I uh I don't do well with other people telling me what to do or micromanaging me. You know, if I get someone who says, okay, here's the objective, go do it, I'm a happy girl. I can do that, I can support people. Um, I'm good at creating systems and processes and getting things the ball across the finish line. And I have worked with people, even in our expert printer online world, helping them grow their seven-figure businesses. But by and large, I need to be the one driving the bus because um I just really the bottom line is I don't suffer fools well. And um, and and I often think, rightly or wrongly, I believe most often rightly, that I have an a better way or a a great idea and therefore want to do it my way. And that's kind of pretty much why most people become entrepreneurs, is because they want to do things their way, they have the ideas, they want to implement it, how they want to see it done. Um, so yeah, that's that's the bulk of it. And and just the whole, I've been an entrepreneur way too long to put up with nine to five and having to, you know, wear high heels or anything like that. Not that I would, but um that kind of thing. Uh I just, yeah, I haven't got the patience for death by meeting and and bureaucracy. It just I can't do it. I don't have the time in my life for that. So yeah, yeah. And it's it's it's probably unfortunate because there would have been times in my life and in my entrepreneurial journey where I would have made more money had I stayed in corporate. Uh, but I would have had less of what I call a story life. Um, you know, really cool stories to be able to tell.

Beverley Glazer: 7:58

And you've come up with some pretty, real cool stories. I have a lot of stories. Yes. Tell us about being a digital nomad because that's a big story.

Jannette Anderson: 8:10

Yeah. Well, I've I've always been kind of interested in travel. I traveled through Central and South America for seven months by myself in 2006, and uh first uh, like I said, for seven months. Um, and I've traveled so far in about, I don't know, I think I'm at 39 or 41 countries. Um my, which is not as many as I would like, and mostly because I tend to stay stuck in the north-south time zone because of client work, but um uh I became a permanent digital nomad about 10 years ago. I had tried variations on the theme. I had a home and roommates and so forth, and I tried going away and I would have issues with the roommates. The last time I came home, they had done about $25,000 worth of damage to the house. So I ended up, that was kind of the straw that broke the camel's back. It's like, okay, I had tried renting the house out while I was gone. I just didn't like paying for two places at the same time, you know, where that that was always frustrating. Uh, so I did a lot of different traveling and digital nomad work. I almost always work when I travel. Uh but the last time was about 10 years ago, and finally it was like, okay, nope, got to sell the house, cannot do this, uh, and go full time. So I sold my home, everything I own. I had over the course of a year two garage sales, and in one I sold $14,000 or $1,400 worth of stuff and $1,200 in the other. And I only had five items over $10 in both of those. So as you can tell, I had a lot of stuff. I do what I called power nesting, just kind of this side of hoarding when I got my first home because I had moved a lot when I was a kid. I moved 29 times in the first 27 years of my life. So when I got my home, I power nested. So when I sold my home, I had a lot of stuff to get rid of. Um, and it was a really interesting process of letting go of, you know, we get to a point where our stuff owns us. And in fact, the last when when I had that experience of coming home and I decided I was gonna sell my house, I looked around my home and I had these big, huge plants. I love plants, and I had these big, huge trees, and I looked at them and I burst into tears, but my plants, and and I kind of stopped myself and I laughed and I said, seriously, you can't have your ideal life because of a ficus. Really? That's what's gonna stop you. And so I'm pretty sure there's plants other places. So I sold my house, everything I owned, downsized, everything went from a 2400 square foot three-bedroom, three-bathroom, very full home to a 10 by 10 storage unit. Now I've got it down to a five by 10. And now I for the past year, so I've done everything from rent places short-term, roommates, um, you know, Airbnbs, travel, various different kinds of digital nomadic. This past year I've been house and pet sitting, mostly in Western Canada. Um, and so I haven't paid rent or mortgage for almost a year, which is very nice. Um, and had lots of different lovely pets to cuddle with that I don't have long-term responsibility for. So that's good too. But it's also a fairly disruptive lifestyle. Like every month or so you're moving, you have to set up your office and get established in a new town or a new location. So it's got definite pros and cons. Most of my friends think I'm crazy. Um, but it suits me and it fits where I'm at now. How did you discover ageism? Oh, it I I notionally knew it was a thing, right? But I was on the marketers cruise, uh, which I had been on a number of times, and and I was up at a networking event called Pizza and Prophets, 10 o'clock at night. And uh someone, I was in a group of five guys, and someone asked me, What do you do? I'm mid-sentence answering him, and he turns and starts talking to someone else. And I think what a jerk. So I excused myself and go to the next group, and same thing happened. And so I thought, Beverly, I thought, okay, well, maybe it's me, maybe I'm not showing up. But you know, I have blue hair and polka dot glasses, and I'm pretty big and in large and in charge. So nope, it wasn't that. It wasn't that I wasn't energetically present or showing up. So what was it? I got curious and I started to observe every person over 60 on that cruise, and at that time, that was 2020, it was about 10% of the people in this marketer's cruise. There's about 450 people there on the cruise all uh together. And uh they were overlooked, they were kind of dismissed, they were not included, and literally the gray-haired women uh were literally invisible, not seen. And uh, and and frankly, that just really pissed me off. Uh, because you know, I've been the subject of sizism, I'm a big woman, um, sexism, you know, I have not gotten jobs because of being a woman or not gotten promoted, not gotten a job because of my size, literally told you're not credible because you're too large. This was by by the way, from a uh sales VP who was 300 pounds and five foot five. Um and and so I I've had my share of isms, but this was like one too many. So I decided to really start to investigate it and see, you know, what's going on? Why is this such a big thing? And it's huge. You know, 65% of North Americans can't afford to retire. If 65% of the population had cancer, the world would be up in arms and governments would be mobilizing. But 65% of the population, because we are older, not able to afford the life that we want, or you know, anywhere from food and housing, the insecurity to just not being able to live the life we want. And no one's doing anything about it. Um, because we're pretty much dismissed and overlooked and undervalued. And so I decided not on my watch. That's not that's not okay.

Beverley Glazer: 14:20

No, it's not okay. But how do you help women who really feel that you know they have been dismissed and they're out of the market and and they should be retired and they should have the money to be able to support themselves and all the guilt and shame that goes along with it, what would you tell those people?

Jannette Anderson: 14:43

Oh, Beverley, that's a brilliant question. Uh, first of all, I'd say stop shooting on yourself. Secondly, just because someone says it doesn't mean it's true, and just because it's in your head doesn't mean it's true. Our internal ageism is as damaging as the external ageism, and sometimes more so because it's insidious. So I would say, first and foremost, you are not done. Uh, you are not irrelevant, you are not um without value, you have tremendous value, experience, expertise, wisdom, um, and and skills that the world needs. Um, you have a contextual perspective that younger generations don't have, and that especially nowadays, we need because we're repeating history in some ways that are very scary. And without older people stepping in and saying, hey, this can lead us here, we're gonna go down a path that's not good for humanity. So we're needed on all different levels. Plus, you have skills and abilities and heart that the world needs. There's there's a problem or problems that you solve that someone needs solving. So uh I would say forget all of what you've been told about the shoulding. Uh, as far as the shame, that's a very real thing. Because, like I said, 65% of us, and I'm in that group, can't afford to retire. And of the 35% who can, by the way, they're super affluent, they currently hold um 80% of the wealth in the world. Boomers and Gen Xers right now hold 80% of the wealth in the world. First time in history that's been the case. Um, many of them are choosing not to retire because they want purpose and meaning and to continue contributing and to stay vital and healthy. So if you're part of that group, don't apologize for taking up space. Continue to contribute, create meaning and purpose. It is critical to you living a happy, healthy, older uh chapter of your life. If if you want to and need to earn, then by all means, do. You got to get in all likelihood entrepreneurial, um, because good luck getting a job. Ageism in corporate America is alive and well, corporate the world. Um, and and so it's challenging to get a job like that to with a capital C. So think about other options: side hustles, part-time businesses, creating a nonprofit, uh, creating your world empire, partnering with people. There's so many options, but you are going to need to get help to shift your mindset from who you've been to who you can be. That's one of the biggest challenges and changes for people now. And help with figuring out how to do that practically in the world right now.

Beverley Glazer: 17:28

Well said. What would you tell someone who wants more income and doesn't know where to start? You know, like uh they're out of it. Where do you start?

Jannette Anderson: 17:38

Okay. Well, I would that's part of why I created the Clarity Compass course, is exactly that question is where a lot of people are at. They're they're going through an identity crisis. Who am I now that I'm not the CEO or the stay-at-home mom or the accountant? Because we often mistakenly think our purpose is what we do. I don't think that's the case. I think our purpose or our why, why we do what we do, is the intersection of what we're healing from the past and what we long for for the future for ourselves and others. So, what we're healing from the past, what we long for for the future. And when we know our why, then that informs what we do, how we do it, and how we live into it over the course of our life changes. But I think our purpose stays consistent. So, how you're gonna live into it now is gonna look different than it did before. You're writing your next chapter. So here's the three things that I think you need to do first. One, clarify your vision. What do you want this chapter to look for and let your desire lead you? You've come from a life of shoulds and have to's and taking care of everyone else and expectations and that whole script of, you know, go to school, get a job, climb the ladder, then you retire, have a, you know, get married, have a pick a fence. That whole notion um is what we kind of all grew up with, but it's so not the only experience of life. And in fact, it's a very outdated notion and doesn't apply to most of the younger generations. So, what do you want? What's those dreams that you've put on the shelf and on the back burner? What makes you happy? And for many people, and as I'm asking this question, often I get a really blank stare because they haven't asked themselves this question much in their life. So they don't know. So sometimes, again, it can be really helpful to get someone to help you to bounce that off of, to pull it out of you, to give you some ideas, to say yes, this, not that. Um, but play with the idea of if I have a blank slate because you do, what would I write on that for the next chapter of my life, which by the way, could very well be a third of your life. If you know you're 60 or something, you probably have another 30, maybe 40 years in you. That's a third of your life. So don't think of this as next chapter as something small or trivial. It's a third of your life for many, many people. Um So write it very intentionally. So first, vision. What do I want my life to be? What could this next chapter be about? What would make me happy? Second, your purpose. Why are you here? Whether you think that's God given, uh, you know, this lifetime, just simply something that you want to put your stick in the sand, whatever you're framing around it is, people do better when they hands up a sense of purpose. And it really impacts our mental health to have meaningful purpose pulling us forward. Um so that's very important. And then the third thing is how are you going to monetize that? How are you going to live into it practically? And for that, I really encourage you to. So all three of these need support often because we can't see the label from inside the jar. It helps to get someone to help us see our purpose because we can't quite see it. It helps to have ideas to bounce off of because often we don't know what we don't know, right? So I would say get a course, get a program, get a coach, get a, you know, if you need support with this, get a therapist, but get someone who can reflect back to you what matters to you, not someone who puts their agenda on you. And there's a lot of that. Very important in just uh to be discerning around that, especially in this chapter of your life. So get your vision clear, get your purpose clear, and then how are you going to practically live into that? Is that a business? Is it a nonprofit? Is it a side hustle? You're going to create a mobile lifestyle? What does that look like? And how do you structurally get support for implementing it and creating it? Because chances are good. It's an area of conscious incompetence. You haven't done it before. And so get some support with it. Yeah.

Beverley Glazer: 21:41

Thank you. Thank you, Jeanette. Jannette Anderson is a business expansionist, a digital nomad, and the fiery founder of Maturepreneur World. After realizing that she was unemployable, Jannette sold her house, hit the road, and built a life and a movement to use age as an advantage. Here's some takeaways from this episode. Entrepreneurship is a strategy for freedom and financial resilience. Retirement is outdated. You can always continue to do some work that you love. Entrepreneurship is the fastest cure to ageism. If you've been relating to this episode, here's what you can do right now. Name one idea that you've been shelving and give it 20 minutes a day. Ask yourself what negative beliefs about age are actually limiting you. It's all in your mind. And redefine retirement. Work towards a vision for your life, something that you can see in 10 years. For similar episodes on ageism and business, check out episodes 130 and 142 of Aging with Purpose and Passion. And so, Jannette, where can people find you? Please share your links.

Jannette Anderson: 23:00

Thank you so much, Beverley. Uh, first of all, maturepreneur.world. So that's the word mature, and then preneur from entrepreneur.world is the website. Uh, you can reach me on um our YouTube channel, the Maturepreneur Network, Facebook, Maturepreneur World, Facebook Community. And I have a gift for your people if they would like to be go from overlooked to overbooked. It's got some tips and some strategies for how to clarify your why. It's an ebook or a guide that you can use to really help you clarify those things I talked about. You can go to maturepreneur.world slash forward slash uh wisdom to wealth. Wisdom to wealth. And get that free guide.

Beverley Glazer: 23:47

And all Jannette's links are in the show notes. And they're also going to be on my site too. That's reinventimpossible.com. And now, my friends, what's next for you? Are you just going through the motions or are you living a life that you truly love? Get my free coaching guide to keep lifting your life higher. And where do you think that is? That's in the show notes too. You can connect with me, Beverley Glazer, on all social media platforms and in my positive group of women on Facebook. That's Women Over50 Rock. And thank you for listening. Have you enjoyed this conversation? Please subscribe and help us spread the word by dropping a review and sending it to a friend. And remember, you only have one life, so live it with purpose and passion.

Announcer: 24:42

Thank you for joining us. You can connect with Bev on her website, reinventimpossible.com. And while you're there, join our newsletter. Subscribe so you don't miss an episode. Until next time, keep aging with purpose and passion. And celebrate life!