The Portfolio Career Lab

Did My Predictions for 2025 Come True?

In this episode, I run back through my big portfolio-career predictions for 2025 and then I cast a little spell for 2026. You know, set the vibes, summon the universe, see what sticks. It’s reflective, kinda witchy… very on brand.

Ashley Rudolph: Inertia Disguised as Achievement

In this episode of the pod, I sit down with executive coach Ashley Rudolph to explore the quiet crisis playing out inside modern careers: mid-career high achievers waking up in lives they never consciously chose. We dig into Ashley’s concept of utopia syndrome—when our ambition slips into autopilot—and how “inertia disguised as achievement” keeps people chasing roles they don’t actually want. We break apart binaries—girlboss vs. no boss, corporate is dead, personal brand is dead, etc—that we believe flatten our choices at the exact moment work is becoming more multidimensional, and we reframe portfolio careers as a means of identity vs income diversification.

The Hamlins: Getting in Front of the Camera

In this episode, I sit down with my former clients Sarah and Brendon Hamlin, the husband-and-wife team behind Hamlin Creative, to talk about what it really takes to evolve an established business in the digital age. After more than a decade of running their video production company, they decided to push beyond referrals and their reputation to experiment with growing their reputation on a new channel—LinkedIn.
We explore what it’s been like translating years of behind-the-scenes expertise into a public voice, learning to engage their ideal audience through authentic storytelling. Sarah and Brendon share how they’ve navigated imposter syndrome, opened up to vulnerability, and turned transparency into a growth strategy.
We also talk about the power of their partnership—how their complementary strengths fuel both creativity and trust—and how building a business together has deepened not just their storytelling, but their marriage.

Geoffrey Colon: AI Ate Our Jobs (And Our Sense of Purpose)

In this episode, I sit down with Geoffrey Colon to talk about how professionals can move through the stages of grief after job loss and channel that uncertainty into creativity and new beginnings. We dig into how the world of work is shifting toward smaller, more independent ecosystems—and the need for new support systems and policies to match.
We also explore the erosion of loyalty in corporate culture, the ripple effects of layoffs on both employees and customers, and why short-term thinking is eroding long-term resilience. Geoffrey warns of a “slow erosion” inside companies that undervalue builders and overvalue managers—a pattern that feels eerily familiar in the age of AI.
We wrap with a hopeful look at the next era of the creator economy: one grounded in depth, direct connection, and creative sovereignty.

Sarah Hanson: Writing a Memoir-in-Verse

In this episode, poet and truth-teller Sarah Hanson joins me to talk about leaving a successful 15-year run in corporate to write her debut memoir-in-verse, Conjuring the Hurricane. Sarah opens up about surviving domestic violence, living through and processing profound grief, and choosing to write about these experiences with both honesty and gentleness.
 

Bree Groff: On Making Work Fun

In this episode, Bree Groff joins me to talk about ways we can make work feel more human and joyful. As the author of the recently published book Today Was Fun and a seasoned change strategist, Bree brings a fresh perspective to the show regarding how both individuals and organizations can embrace ambiguity, build resilience, and actually enjoy the process of transformation.

Lindsey Lerner: Field Notes from the Work and the Wild

In this conversation, I chat with writer, photographer, and community builder Lindsey Lerner to explore the launch of her year-long project Field Notes from the Work and the Wild. Lindsey shares how her background in anthropology, photography, and storytelling informs her work documenting the often-overlooked process behind our creativity.
We chat about :
The origins of Field Notes and her drive to celebrate everyday work, not just the big wins
Lessons from a decade of working in the music industry 
Art in business
What it means to find your creative flow, and 
The role of community in shaping meaningful work
Lindsey even opens up about the realities of pursuing creative projects alongside practical survival work, launching a GoFundMe to support her field year, and her hopes for bringing people together across geographies and disciplines.
 

Jillian Reilly: Redefining the Rules of Adulting

In this episode of The Portfolio Career Lab, I sit down with author and change strategist Jillian Reilly to explore what it really means to give yourself permission to architect a career on your terms at any age.
Jillian shares a bit about her new book The 10 Permissions: Redefining the Rules of Adulting for the 21st Century and chats with me about why so many of us are still waiting for a “green light” before pursuing our deepest desires.
Together, we discuss:
Why permission is a lifelong practice, not a one-time decision
How our conditioning to conform keeps us stuck
The radical act of listening to your “pesky inner voice”
Redefining success (beyond the concepts of accumulation, ownership, and status), and
Preparing the next generation of adults to thrive in a world without a career template
And if you enjoyed listening to this episode, go support Jill by buying her book over on Amazon!
 

Shaina Feinberg: Filmmaking, Family, and Finding Your Voice

And.. we're back for season two!
In this season’s opener of The Portfolio Career Lab, filmmaker, writer, and mother Shaina Feinberg joins me for a conversation about creating art inside the chaos of motherhood, the unlikely mentorship she found with legendary actor and director Joan Darling, and her upcoming documentary None of This Matters.
I hope this conversation moves you the same way it moved me!

Anna Mackenzie: Redefining Plan A

Are you a regular listener of the show? Do you want to shape the conversation for season 2? Fill out this quick survey and help me and the production team ideate for next season's guests and episode lineup. (And if you can, leave a review of the show on Apple or Spotify too!)
In this final episode of the first season, I sit down with my friend Anna Mackenzie. Anna has built a portfolio career that blends digital products, global mentoring, writing, and fractional advisory work. We talk about how she transitioned out of her first business and into portfolio life post-COVID, the tension between freedom and burnout, and why structure is a non-negotiable for sustainable autonomy as a portfolio careerist.
We also dig into the emotional side of this path — the grief of leaving our old identities behind, how the global conversation around job security is shifting, and what it means to build a career that’s rooted in self-expression, not just monetization.