The Portfolio Career Lab

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.
 

Alex Huhn: Building a Minimum Viable Brand

In this episode I sit down with Alex Huhn, a marketing strategist who’s built a portfolio career that blends the stability of a W2 with a growing marketing studio of real estate clients. We talk about how he navigated the messy middle following a layoff,  the Dream 100 strategy w, and what shifted once he stopped chasing the content treadmill and started building a “minimum viable brand.”

Shaina Anderson: Is Fractional is the Future?

In this episode I sit down with Shaina Anderson, a former Chief of Staff at Yelp and startup operator, as she shares her journey into the world of portfolio careers and the genesis of her business Hello Generalist. We chat the rise of fractional work, the difference between executive advisors and hands-on generalists, and why not every generalist is created equal.
Interested in fractional?
Go check out Shaina's program  Manual Override which starts this Summer!

Jamie Lee: Person Market Fit

In this episode of the pod, I sit down with Jamie Lee, founder of JME Lab, to unpack the evolution of her portfolio career and the strategic framework she's built around her business around (Jumpstart, Mobilize, and Elevate!). Jamie shares how she’s scaled her business through a thoughtful mix of consulting, fractional advisory, teaching, and one-on-one coaching engagements.
From her early days at companies like Sony, EA, Walmart, and Nike to supporting scale-up brands like Everlane and Vital Proteins, Jamie reflects on how her corporate experience shapes her current business building mindset. She dives into how her time is now structured and how she thinks about AI adoption for leaner startups.

Harry Siggins: What's a Chief of Staff?

In this episode, I sit down with Harry Siggins, a former Chief of Staff turned workshop facilitator helping growth-stage companies. After five years acting as the strategic Swiss Army knife for startup CEOs, Harry stepped off the always-on hamster wheel and into a portfolio career focused on what gives him the most energy: designing high-trust, high-impact workshops!
We unpack what the Chief of Staff role really entails, why the role has exploded in the growth-stage tech world, and how Harry discovered that the real value wasn’t in “doing it all,” but in helping leadership teams actually get aligned and make decisions that stick.
Harry shares why he’s betting big on workshops as the human antidote to AI overload—and how even non-tech companies are hungry for them. We also talk candidly about the limits of fractional Chief of Staff work and what it takes to design a portfolio career around the role.
If you’re considering the COS role or a founder craving a business strategy reset without another bloated offsite, this episode is for you!
Check out Harry’s work at one two growth

Janel Abrahami: Don't Hate the Player, Hate the Game

In this episode, I sit down with career coach, speaker, and future of work thought leader Janel Abrahami whose thought leadership has been featured in CNBC, Business Insider, Girlboss, and more. Janelle shares how a career crisis in 2020 led her to create a portfolio career—one that combines coaching, content creation, speaking, and more.
We unpack how she navigated the ‘messy middle’ of career transitions, how she leveraged content to build a powerful personal brand, and why layering income streams is key to portfolio career success. Janelle also gives a candid take on the personal brand debate—do you really need one?—and how she strategically approaches TikTok, Instagram, and LinkedIn to drive opportunities.
Plus, she shares an exciting preview of her revamped career transition course Pivot with Purpose and her journey toward publishing her first book. If you’ve been wondering how to make content work for your career (without burning out) or whether a personal brand is truly necessary, this episode is for you.
Check out Janel's course here: janelabrahami.com/pwp

Jori Bell: Why PMs make great portfolio careerists

In this conversation, I sit down with Jori Bell, a product coach whose product experience includes companies like SoundCloud, Spotify, and Audible. Jori chats with me about her transition from consumer tech. We discuss the challenges of personal branding, imposter syndrome, and balancing multiple roles while trying to maintain focus. We also explore experimentation, lifelong learning, and how small steps lead to bigger impacts in an unconventional career. 
For more information on Jori, check out her website: https://www.joribell.com/

Danielle Rogers: The Path to Self-Publishing

In this conversation, I sit down with Danielle Rogers, founder of Cleverly Corporate and SVP at Truist, to discuss her journey navigating an incredibly challenging 2024 and how it led her to build a portfolio career.
Danielle shares the highs and lows of 2024—including getting engaged (and later calling off the engagement), experiencing a layoff that... wasn’t quite a layoff, and dealing with personal losses. Despite these challenges, she channeled her energy into writing her very first book, The Job is Yours: Seven Steps to Land Your Next Role After a Layoff, a practical guide to job searching based on her decade-plus of experience as a hiring manager.
We explore how Danielle transitioned into a portfolio career after realizing the importance of diversifying her income streams, why she founded her business Cleverly Corporate, and her process of self-publishing her book.
This episode is a must-listen for anyone navigating career uncertainty, layoffs, or looking to build a sustainable and fulfilling career on their own terms.
If you want to connect with Danielle or learn more about her work, you can find her at CleverlyCorporate.com or you can purchase her book on Amazon!