Jo Barnes: Turning Experience Into Freedom-Funding Micro Hustles After 50✨The Career Pivot Playbooks Series
Jo Barnes: Helping people over 50 turn experience into freedom-funding micro hustles that support travel, purpose, and choice.
This Career Pivot Playbook features Jo Barnes, a long-time digital nomad and online entrepreneur who has spent the past 15 years building location-independent businesses while travelling the world.
Jo’s path began with a single leap. Fifteen years ago, she and her husband sold everything they owned, packed three suitcases, and left the UK with their four-year-old daughter to house-sit in Cyprus, with no fixed plan, just open minds.
What followed was a decade of building and experimenting online. Membership sites, digital products, online courses, coaching, blogging, affiliate marketing, and live trainings all became part of Jo’s evolving portfolio, funding years of travel and a life lived across countries.
Between 2010 and 2015, Jo generated well over seven figures through online education and community-led businesses. She later pivoted into e-commerce, building and scaling an Amazon brand that sold over 84,000 products in its first year, before successfully exiting the business in early 2020.
Jo’s career never followed a single blueprint. It evolved through learning on the job, problem-solving in real time, and staying willing to look like a beginner again… even after years of experience.
More recently, Jo discovered Substack, which has become the central platform for her personal brand, The 50+ Nomad Club. It’s where she now shares stories, practical guidance, and perspective with people over 50 who want to build micro hustles that fund freedom, travel, and purpose.
Rather than chasing scale for its own sake, Jo focuses on alignment. Audience trust, clear offers, and businesses that support life (not the other way around) sit at the centre of her work.
This Playbook explores how long-term experimentation, audience ownership, and experience-led micro hustles can come together to form a flexible, sustainable portfolio career… proving that reinvention doesn’t have an expiry date.
About Career Pivot Playbooks
A public archive of modern career blueprints…
Most careers no longer follow a straight line.
People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.
Career Pivot Playbooks is a weekly series documenting how professionals are building resilient, future-ready careers, with professionals often using Substack alongside research, consulting, teaching, creative work, or operating businesses.
The focus isn’t outcomes.
It’s about how careers are shaped in practice.
About Jo
Jo Barnes is a long-time digital nomad and online entrepreneur who has spent the past 15 years building location-independent businesses while travelling the world. Through her work as The 50+ Nomad, she helps people over 50 create micro hustles that fund freedom, purpose, and a life of travel.
On Substack, Jo shares practical ideas, real-world examples, and what she’s building in real time—showing how simple, experience-led micro hustles can support a flexible, freedom-first lifestyle.
You can follow her work here →
Jo reflects:
“Can you share a bit about your professional background and the path that led you to where you are today?”
Hello! My name is Jo and 15 years ago, my husband & I scooped up our 4 year old daughter, jumped on a plan to Cyprus to house sit for some friends and haven’t looked back since!
I started building online businesses so we could continue travelling and over the years have had membership sites, digital products, online courses, ecommerce, blogs and everything in between!
The businesses have funded our travels for over a decade and afforded us the opportunity to raise our daughter in Phuket, Thailand. (She’s now at college in London)
A few years ago we had fantastic success with an e-commerce brand selling on Amazon and sold that business in early 2020. From there I started blogging for a while and most recently discovered the wonderful Substack!
Right now my brand The 50+ Nomad helps people over 50 to build micro hustles that fund freedom & travel. Plus I’ve launched another Amazon business selling fun travel products. It’s going to be an interesting year!
“What sign, moment, or slow realisation told you it was time to diversify — and what did you have to push through to actually act on it?”
The biggest pivot moment I had was 15 years ago, living in the dreary UK and desperately wanting to travel. Thankfully I had a broad minded husband and some good friends who were already living my dream life.
My friend recommended I read ‘The Four Hour Workweek’ by Tim Ferriss, which I practically inhaled. So when the same friend asked us if we wanted to house sit his apartment for 2 months in Cyprus, ’No’ wasn’t an option!
We sold everything we owned in the house we were renting at the time, packed up 3 suitcases, and with the $1000 we’d made from selling our worldly goods and our 4 year old under our arm, headed out into the great unknown.
“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”
It would have to be ‘problem solving’.
When I started in 2010 I knew nothing about the online world, so it was a super steep learning curve.
I remember being in the Warrior Forum (blast from the past) and finding out that all url’s started with ‘http://’. I thought they all started with www! (A chap on the forum told me maybe online marketing isn’t my thing…)
I started with webinars learning from the great Steven Essa, launched a membership site (using a platform called Membergate), and generated $117k in 7 days. I created digital courses, added affiliate marketing to the mix, dabbled in coaching and ran lots of ‘live trainings’, what are now called ‘cohorts’.
Between 2010 - 2015, I generated well over 7 figures in all of the above, and then we decided to try our hand at e-commerce selling physical products.
My husband & I created a brand in the cooking niche of all things (neither of us can cook) and sold over 84,000 digital cooking thermometers at $15 a piece in the first year!
We eventually sold the business in early 2020 and I decided to try my hand at blogging until I eventually found Substack.
Pretty much everything was learning on the job and never giving up. If only I’d had AI in the early days…. 😉
“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”
I’ve mentioned a couple of times that I’ve recently discovered Substack which highlights its importance in my future goals.
One of the challenges for most new solopreneurs online is audience building and list building. Substack takes care of both of those things for you while allowing you to share your true voice.
Unlike some of the other social platforms where you have to really play to the algorithms, Substack rewards depth, and engagement. Over the short time I’ve been on here I’ve been able to build some fantastic relationships and it actually reminds me of Facebook back in 2010. Supportive, engaging & community led. Long may it last!
I do still post regularly on my 28k strong FB page, and after all these years I still find Facebook my favourite short form social platform.
But for my new e-commerce brand ‘This Big World’, I’m actually thinking TikTok will be the best place to showcase my products so I’m about to go down that rabbit hole.😳
However, my main visibility platform for my personal brand The 50+ Nomad, will be Substack for the foreseeable future.
“Who is your work really for — and what problem do you solve so well that people are willing to pay for it?”
My work is for people over 50 who believe wholly in Ikigai - the Japanese concept of your reason to jump out of bed in the morning!
They’re smart, capable, often experienced professionals or business owners who don’t want to shrink into retirement, but instead want to travel, explore the globe and create fun and profitable side projects that fund their freedom and keep the brain cells active!
The problem I solve is in helping them turn their passions into profits and showing them ways to translate their wealth of knowledge into creative micro hustles online.
They pay for clarity and simplicity, and for the permission to start later, move at their own pace, and build something that fits their ideal lifestyle. On a practical level, they also come to me to learn how to build the kind of audience that makes a freedom-funding micro hustle possible.
“What turned out to be harder than you expected when you started — and what was easier than you imagined?”
When I first started online undoubtedly it was the tech that held me back. These days it’s become much easier for non tech people to build websites, landing pages, blogs, make videos and everything you need to start and grow a fully fledged online business.
More recently it’s been my ego that’s got in my way. Feeling afraid to look like a beginner again in a world that’s become more overwhelming, more noisy and full of young whippersnappers running rings around us ‘older folk’.
I’m moving past that the more I post, and the more I engage. We have so much talent and experience at our age. We need to let that shine!
“How have you found the journey? What advice/ strategies and tips would you give to others wanting to grow their audiences?”
As I’ve said before, Substack has been a wonderful experience. It’s a great community here and I love chatting and engaging with such interesting people.
It’s also been a breath of fresh air to share my thoughts and stories without worrying about SEO or algorithms.
If you’re just getting started, focus more on notes and engagement than a perfect posting record in the early days. Find people you resonate with, comment, restack and get involved.
If you’re on Substack merely to improve your writing skills, tell your stories and meet interesting people there are no rules.
If you want to monetise, make it clear what you write about and who it’s for from the getgo. No clever publication or article names that mean nothing to anyone but you.
And be patient! Growth comes from trust compounding, not hacks or clever tactics.
“What nearly made you quit, and what actually kept you going?”
I remember very clearly in my first year online deciding it wasn’t going to work. I was building a community, running webinars, launching products, but not much was working.
We were living in my husband’s parents basement (not ideal with a 4 year old) and I went for a walk listening to Tony Robbins in my ear.
When I got back I was so fired up I ran a webinar about not giving up and within 3 months had my first 6 figure week!
“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”
Don’t wait until you feel ready or until all your ducks are in a row as that’s unlikely to happen.
Just start.
Start where you are, with what you know, and put your thoughts, products, services, offers, in front of real people as soon as possible.
Charge earlier than feels comfortable. Learn faster than you think you need to. And build something that supports your ideal lifestyle, not what you think you ‘should’ build.
Stay true to your dreams and know that someone out there needs what you can offer.
“What other platforms, audiences, or income streams are part of your portfolio career — and how do they work together?”
Alongside Substack, I run coaching, digital courses, books, and a physical product brand designed around travel and experience. Each piece feeds the others.
Content builds trust, trust supports sales, products deepen commitment, and everything points back to the same core message around freedom, purpose, and choice!
Over the coming years I hope to grow This Big World into a popular fun & quirky travel brand, continue growing my audience on Substack and publish more books and helpful resources. All while backpacking across the world! 🌎
“Looking back, what’s one decision that changed everything — and what’s next for you?”
The decision that changed everything was undoubtedly the week we decided to sell everything we owned and get on that plane to Cyprus with no onward (or backwards plans).
We knew we wanted a life change and we jumped, with no safety net, and somehow the world caught us.
What’s next for me is to explore every corner of the globe while building a body of work that supports a life of travel, creativity & contribution & inspires others to live their dreams!
Adventure Never Retires!
Links & Resources
https://www.facebook.com/jobarnespage
https://explore.thisbigworld.co/buynow - My Travel Challenge Cards
Related Articles
How to Build a $2,600/Month Business in 12 Months
The 4 Micro Hustles I’m Building This Year (And Why They Work So Well After 50)
The Fastest Way to Fund Your Freedom (Even If You’re 60+ and Starting Over)
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I work as a future-focused career advisor, helping professionals adapt and grow in real time. If this resonates, explore my Substack here →
Katharine from Learn Grow Monetize
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Its interesting how “freedom” goes along with photos of being on a sailboat. 🤔😂