People say they want more freedom… but very few actually design a life that gives it to them.
In this episode, I sit down with Linda Jackson — full-time sailor, digital nomad, and creator of Shellphone Chronicles — who, alongside her husband, lives aboard an incredible 77-foot aluminium yacht as they sail across the Pacific.
Linda has been a digital nomad since long before remote work was “a thing,” running her consulting business from the middle of the ocean, weathering storms, navigating huge passages, and building a lifestyle that most of us secretly dream about but rarely believe is possible after 50.
This conversation is warm, honest, and full of the kind of lived wisdom that only comes from spending years at sea and choosing freedom as a way of life.
What You’ll Learn in This Episode
What life really looks like living full-time aboard a yacht
How Linda built a long-term consulting business from the ocean
The moment she and her husband bought an 80-foot aluminium boat everyone said they were “too old” for
What a 22-day, 4,000-mile ocean crossing actually feels like
The difference between land nomadism and sea nomadism — and why both require grit
How freedom and self-sufficiency take on a whole new meaning when your home floats
The biggest misconceptions people have about living remotely
Safety at sea: weather, pirates, and what really matters
Linda’s advice for anyone 50+ dreaming of a big lifestyle shift but unsure where to begin
Key Takeaway
Freedom isn’t something you wait for. It’s something you create. One brave decision, one new skill, and one honest self-assessment at a time. You don’t have to live on a yacht to live freely… but you do have to give yourself permission to try.
Time-Stamped Guide
00:00 Welcome back + introducing Linda Jackson
00:55 Linda’s life at sea today + her journey through the Pacific
03:00 Becoming a true OG digital nomad long before it was mainstream
04:50 How she built and ran a consulting business from the ocean
07:20 The transition from corporate/startup life to full-time freedom
10:30 What it really takes to find clients, deliver work, and keep a remote business alive
12:00 Life onboard with her husband — roles, teamwork, and trust
14:45 Buying a 77-foot project boat everyone thought was too big, too hard, or too crazy
17:00 The backstory of SV Duende and why they took on such a huge project
20:00 Surviving their first hurricane in Florida
21:45 What a “shakedown sail” is — and why theirs was a 4,000-mile voyage
23:30 Crew, systems, and how advanced tech made a bigger boat easier
26:00 The 22-day crossing to Tahiti — food, routines, and staying sane at sea
31:00 The difference between arriving somewhere by air vs. by water
33:00 Freedom, self-sufficiency, and what long-term travel teaches you
36:00 Safety at sea — pirates, storms, and keeping a low profile
40:00 Misconceptions about cost, skill, and the effort involved
41:30 How similar boat life and land nomadism really are behind the scenes
43:20 Linda’s advice for anyone 50+ wanting a big lifestyle change
45:30 Life plans: Fiji, Vanuatu, the Solomons, and the seasons ahead
47:30 Why Substack feels like the early days of Facebook
48:30 Outro + where to follow Linda
Resources Mentioned in This Episode
● Shellphone Chronicles on Substack — Linda’s beautifully written publication about life at sea
● Erin Mickelson – Nomad Life on Substack
● Benthall Adventures (Kelly)
Join the Conversation
Have a question for Linda about life at sea?
Share it in the comments — we’d love to bring her back for a follow-up episode.
Are you dreaming of your own version of freedom?
Tell me one brave step you could take this week toward your dream lifestyle.
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! 🙏
🎉 Win a $5,000 Dream Holiday as Part of my Brand New Ecom Launch! 🎉
By the way, I’m launching a new brand called This Big World, a collection of travel-inspired products designed to add more fun, curiosity, and adventure to life on the road.
The first release is The Travel Challenge Scratch-Off Deck. 50 playful prompts to help you see the world with fresh eyes, meet new people, and say “yes” to more spontaneous moments. (My sister and I have already had a blast testing a few through Italy!)
To celebrate the launch, I’m giving away a $5,000 Dream Holiday!
✨ Join the Early-Bird Insiders List ✨
As a member of my Substack community, you’re getting first access, before I open this to the public. Join the Insiders List now to be one of the first to grab your deck and secure your chance to win the $5,000 Dream Holiday.
Because life’s too short to travel small! 🌍
