Reletter
Artwork for Nomads 50+ Midlife Recalibrated, Travel Optional.

Redefining freedom, reinvention, and meaning after 50. Inspiration Tuesdays, interviews on Thursdays, city guides on Fridays, and location-independent business ideas on Sundays. Travel optional.

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Substack
PricingFreemiumPublishesDaily
Issues248Foundeda year agoLast Issue3 days ago
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nomads50plus.substack.com
Artwork for Nomads 50+ Midlife Recalibrated, Travel Optional.

Latest Issues

Chasing Maximus with Ryan Maxwell & Chris (Nomads 50+)

Get more from chris kalaboukis in the Substack app

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3 days ago
3

Sunday Spark 37: Curated Tool Directory Business

Build a Valuable Digital Asset by Helping People Find the Right Tools Faster

Every Sunday, The Sunday Spark explores a location-independent business designed specifically for digital nomads, remote workers, and entrepreneurs over 50.

4 days ago
2
Paid

City Guide 49: Oaxaca, Mexico: Culture, Climate, and a Richer Pace of Life

Upgrade for $5/month and access all City Guides, Sunday Sparks & The Upcoming Nomads 50+ Recalibration Companion.

Oaxaca isn’t a destination that shouts for attention. It doesn’t have the beaches of the Riviera Maya, the skyscrapers of Mex...

6 days ago
4
Paid

Ep. 57 Laid Off at 59 and Betting on Himself

In this episode of Nomads 50+, Chris Kalaboukis speaks with Harold Wilkerson, a 25+ year travel industry veteran who made a bold decision after being laid off at 59:

👉 Instead of going back… he bet on himself.

His story isn’t the...

7 days ago
8

Ageism Is Real. Don’t Let It Define Your Next Chapter.

The Unspoken Bias

One of the less discussed realities of becoming a digital nomad later in life is that ageism exists.

Not everywhere. Not all the time.

But often enough that many people notice it.

The digital nomad movement was larg...

9 days ago
18
20

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Authors

The writers behind this newsletter.

  • chris kalaboukis

    Futurist and digital nomad writing about AI, the future of work, longevity, and location-independent living—for builders, founders, and 50+ reinvention seekers.

  • Dr. Debra Kouda

    Mother, wife, and innovative entrepreneur

  • Karen Cherry

    Aussie business owner. $105K+ revenue on Substack. Secret tree hugger. Writes Pubstack Success for Substack creators and The Rotten Apple newsletter for food industry professionals.

  • Sherry Chidwick, Storyteller

    Sold everything to become full-time global nomads in midlife. Trading comfort for peace. Relearning life, unstuck, and writing the stories. Off to learn from the world and love people like Jesus taught. It's never too late to try something new.

  • Lauren Gabrielle Foster

    Writer and guide for women in midlife and beyond. At 60, I live as a global nomad, witnessing life firsthand. I share grounded reflections and embodied practices rooted in real life, real bodies, and the sacred ordinary.

  • Ryan Maxwell

    I work with men who have built the life they wanted and can't shake the feeling that something is missing. I help them determine where they are, how they got there, and what to do about it — so they don't have to figure it out alone.

  • Pete Cataldo

    Midlife doesn't have to be a crisis. LevelUp into your best decade yet: More time, better health, life on your own terms. I've got the cheat codes \ud83c\udfae

  • The Midlifepreneur

    I’m Stacy Spark, The Midlifepreneur and Income Architect for women 50+ who are done with the workforce and ready to turn the experience they already have into income that fits their life.

  • The Calm Traveler ( Harold )

    I spent 25 years managing travel programs for Fortune 500 companies. Now I help travelers over 50 plan trips with fewer surprises and more time for the trip itself. Practical planning. Smart pacing. No stress before you leave home.

  • Sofia - Chief Untangler

    I've untangled my life enough times to have opinions about it. Mostly because I tied myself into most of the knots first. Three continents \ud83c\udde6\ud83c\uddf9 \ud83c\uddff\ud83c\udde6 \ud83c\uddfa\ud83c\uddf8, three rebuilds. One forced at 29, one chosen at 42, one forced at 60.

  • The No F*cks 40's Club by AFW

    The space for women who are turning 40 and running out of f*cks to give in the best possible way. Brought to you by Dr. Thomai Roi and her work at Arguably Feral Women.

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