Carolyn turned teaching English into a way to build a life abroad. We talk about the realities of long-term travel, the parts of living globally that rarely make it onto social media, and how she built work around the lifestyle she wanted.

Unexplored Paths explores careers through conversations with the people walking them, so you can figure out what you want from yours.

Ask yourself these questions as you listen

• What parts of the digital nomad lifestyle appeal to you, and which would wear you down?

• What would you change about your work to have the freedom to live abroad?

Guest Links

• Carolyn’s Instagram

• Carolyn’s Polarsteps

Explore further

Curious about becoming a digital nomad? The companion guide explores the realities of building a location-independent life so you can understand the tradeoffs, test the lifestyle, and explore ways to work abroad. It includes certification resources, housing and community-building strategies, and a framework for translating your existing experience into remote opportunities.

Carolyn's Guide: Digital Nomad Strategy

There aren't enough lifetimes to try every career. So we talk to the people walking them.

Anna left McKinsey to buy and operate small businesses.

We talk about what it's like to run a business in an industry you know nothing about, how she prioritizes when everything needs her attention, and why execution skills can transfer across industries.

Unexplored Paths explores careers through conversations with the people walking them, so you can figure out what you want from yours.

Ask yourself these questions as you listen

• Which skills from your current career could transfer to a completely different industry?

• How much uncertainty would you trade for ownership?

Guest Links

• Anna’s LinkedIn

• Mention you found her through Unexplored Paths.

Explore further

Curious about buying or operating a small business? The companion guide goes deeper into small business acquisition so you can evaluate potential companies, understand their core revenue drivers, and prepare for the realities of operating a business. It includes evaluation frameworks, search criteria, and outreach templates for connecting with business owners.

Anna's Guide: SMB Acquisition & Operations

There aren't enough lifetimes to try every career. So we talk to the people walking them.

Wanz went from making music in his spare time to winning a Grammy for Thrift Shop with Macklemore & Ryan Lewis.

But a breakthrough doesn't automatically change your career.

We talk about what happened after the spotlight, why he kept a day job while making music, the mistake he still thinks about, and what it takes to build a creative career when success doesn't look like you expected.

Unexplored Paths explores careers through conversations with the people walking them, so you can figure out what you want from yours.

Ask yourself these questions as you listen

• How much financial stability would you need to keep pursuing your creative work?

• What would you do if the success you imagined didn't arrive in the way you expected?

Guest Links

• Wanz’s website

• Search "WANZ" to find his music and upcoming shows.

Explore further

Curious about balancing a creative music career with a day job? The companion guide explores ways to support your creative work while maintaining financial stability. It includes frameworks for presenting your music, translating technical skills for other roles, and pitching to music supervisors.

Wanz's Guide: Music Career with a Day Job

There aren't enough lifetimes to try every career. So we talk to the people walking them.