What if the next chapter of your life could be your best yet?
You don’t need a million-dollar idea or decades ahead of you to create freedom. You just need to decide, start, and take that first step.
In this powerful co-interview, Jo Barnes (The 50+ Nomad) and business coach Shandra Moran (The Transit Lounge) share the real stories, mindset shifts, and practical strategies that can help you turn what you already know into an income stream that gives you flexibility and freedom.
Shandra has helped countless women 40+ grow their service-based side businesses into reliable income. Jo has spent the past 15 years building digital businesses while travelling the world. Together, they reveal the opportunities (and the hurdles) of starting midlife, and why it’s absolutely not too late.
What You’ll Learn in This Episode
Why action-taking matters more than strategy in the early days
How to start small (“coffee money”) to build confidence and momentum
The top three hurdles most new entrepreneurs face, and how to get past them
Practical steps to package your skills into a service people will pay for
Why niche clarity comes through doing, not overthinking
The myth of “too late” and why midlife is the perfect time to begin
Key Takeaway
Freedom doesn’t require a million-dollar idea or a perfect plan. It begins the moment you decide to start, take one small step, and give yourself permission to learn as you go.
Time-stamped Guide
00:00 Welcome + what it means to be “geoflexible”
05:00 Jo’s journey from house-sitting in Cyprus to building online businesses
11:00 Shandra’s career pivot: from radio executive to business coach
16:00 The biggest hurdles: confidence, marketing, and money
23:00 Why starting small builds belief and momentum
31:00 Finding your niche through testing, not theory
41:00 The myth of “too late” and why freedom can start at any age
50:00 Future opportunities with AI and online business models
56:00 Final thoughts: take action, find community, and trust yourself
Resources Mentioned in This Episode
Shandra’s coaching & resources: thetransitlounge.com | LinkedIn | Facebook
Jo’s writing, courses & community: the50plusnomad.com
The 4-Hour Workweek by Tim Ferriss — the book that sparked Jo’s digital nomad journey
Tim Ferriss’s reminder: “people don’t want millions, they want the freedom experiences they think millions can buy”
The Artist’s Way by Julia Cameron — on being willing to “suck” first before becoming great (see quote below)
Steven Bartletts podcast interview with Ray Dalio (sorry I mistakenly said Ryan Moran on the podcast) — where he shared his framework for success: meaningful work + meaningful relationships + money
“It is impossible to get better and look good at the same time. Give yourself permission to be a beginner. By being willing to be a bad artist, you have a chance to be an artist, and perhaps, over time, a very good one.”
Julia Cameron
Join the 50+ Nomad Club
If you’re ready to start building your dream lifestyle, whether that’s travelling full-time, living part-year overseas, or creating more freedom at home, you’ll love The 50+ Nomad Club.
Inside, you’ll get practical strategies, inspiration, and a supportive community of like-minded adventurers who believe adventure never retires.
Download My Free Guide
📖 How to Become a Digital Nomad in Your 50s & Beyond
This practical guide will help you map out your portable income, choose the right business model for you, and start planning your first nomadic leap with confidence.
Join the Conversation
What’s one skill, passion, or idea you’ve been sitting on, and what’s the smallest step you could take this week to test it out?
Share it in the comments below, your step might spark someone else’s freedom journey.
Loved this episode? The biggest compliment you could give me, would be to share it, restack it or send it to someone else who would love it! Thank you so much! 🙏
