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.

Leah started as a Starbucks barista and one seemingly unrelated decision led her to a role in corporate sustainability.

We talk about the coincidences that led her to corporate sustainability, why the role doesn't require a sustainability degree, and what she wishes she knew before entering her role.

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 can the projects, people, and activities in your life create opportunities you don’t see yet?

• Which experiences or skills are you building now that might become useful later?

Guest Links

• Candidly Said Journals

Explore further

Curious about corporate sustainability? The companion guide goes deeper into the field so you can understand the work, identify transferable skills, and explore how to move into sustainability without a specialized degree. It includes a framework for starting a sustainability project at your current job, resources for relevant corporate tools, and networking templates.

Leah's Guide: Corporate Sustainability

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

Cat built her life around freedom.

Instead of following one career path, she works multiple jobs and continues building her own projects because freedom is one of her highest priorities.

But freedom has tradeoffs. We talk about why Cat stopped putting her heart and soul into building other people's businesses, how she decides what to pursue next, and the financial consequences of choosing autonomy over stability.

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 does a successful career look like to you?

• How do you want to balance autonomy and financial security in your career?

Guest Links

• Cat’s Instagram

• Find Cat's classes through Pilates Studio of Reno on the MindBody app.

Explore further

Curious about building a multi-career life? The companion guide explores the choices, tradeoffs, and practical considerations behind this path so you can evaluate whether it fits what you want from your career. It includes a self-directed lifestyle exercise, a contract template for formalizing client agreements, and two pathways for exploring Pilates instruction, along with practical steps for exploring independent work in other fields.

Cat's Guide: The Multi-Career Life

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

Logan thought he was going to dental school. Instead, one conversation changed the direction of his career.

We talk about what physician recruiting looks like, why sales skills matter more than medical knowledge, and the financial lessons he wishes more doctors learned earlier.

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 do you want your career to give you beyond a job title?

• What careers exist that you haven't even considered because you didn't know they existed?

Guest Links

• Logan’s LinkedIn

Explore further

Curious about physician recruiting? The companion guide goes deeper into the field so you can evaluate the career, understand how to get started, and explore whether it could be a path for you. It includes an example of how Logan uses AI in his workflow, tools you’d need to know for the job, and resources for breaking into the field.

Logan's Guide: Physician Recruiter

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