The Portfolio Career Lab

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.

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.

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.  

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.

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.  

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!  

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!

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.  

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.”

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!

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.

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

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

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/

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!

In this conversation, I sit down with Bryon Majusiak, a former mechanical engineer at Google and Blue River Technology, to explore his incredible work with Rally for Rangers, a nonprofit organization dedicated to equipping park rangers around the world with the tools they need to protect some of the planet's most vulnerable ecosystems. Bryon shares his journey from being a participant in a single rally to becoming deeply involved in the organization’s logistics and mission. He reflects on how donating motorcycles to park rangers in remote regions like Mongolia, Namibia, and Nepal has transformed their ability to protect wildlife and conserve natural landscapes. Bryon highlights powerful stories, including rangers cutting month-long patrols down to days, addressing illegal activities, and even rescuing orphaned bear cubs. We also discuss the broader implications of balancing a career in tech with deeply meaningful volunteer work. Bryon opens up about how his sabbatical helped him reassess his values and protect time for his passion projects as part of his broader portfolio career. This episode is a must-listen for anyone interested in conservationor finding purpose in unconventional career paths. 💡 And if you want to support Bryon and Rally for Rangers and the inspiring work this organization does, you can donate directly at RallyForRangers.org. 

In this conversation, I sit down with Coach Ellun, a former scientist turned burnout expert, to explore her journey from academia to entrepreneurship and her mission to help others navigate the challenges of modern work. Ellyn shares how her personal experience with burnout during her PhD program led her to research and develop practical strategies for recovery, ultimately inspiring her transition into coaching. We dive into the roots of burnout, including the societal pressures of high achievement, the myths of work-life balance, and how emotional misalignment often manifests as burnout. Ellyn unpacks her proactive approach to stress management, emphasizing the power of systems, self-awareness, and sustainable self-care practices. She also reflects on the unique challenges faced by portfolio careerists and high achievers, offering actionable insights for thriving in unconventional work models.

In this conversation, I sit down with Dave Kang, entrepreneur and brand strategist, to explore his bold experiment in building an “octopus-style” portfolio career. Dave shares how his journey began with a corporate layoff and a transformative sabbatical, leading him to embrace generalism and launch multiple "tentacles" of work—from brand strategy consulting to e-commerce and even ambient music production. We dive into the philosophy behind his unique approach, including the importance of integrating work and life, the challenges of balancing multiple revenue streams, and the criteria he uses to decide which projects to pursue. Dave also discusses his vision for a future where generalists are valued, sharing his goal to create a community of portfolio careerists and, ultimately, innovation teams built entirely from generalists. From redefining work-life integration to challenging the specialist-driven job market, we cover why portfolio careers offer a compelling alternative for those seeking fulfillment, variety, and purpose in a fast-evolving world of work. P.S. - Check out Dave's Life-at-a-Glance motivational calendar 

Through a short and sweet guided moment of stillness, Brie invites you to reset, recharge, and reconnect with yourself while inviting in the change of the seasons. Let this be your permission slip to step back and step into 2025 with renewed clarity and intention after some R&R for the remainder of the year. Take a deep breath and join us. You deserve it.

In this episode, I sit down with Paige Hewlett, marketer, founder, and VP of Marketing at Mobius Risk Group, to explore her journey through a portfolio career and the creation of Margo, a SaaS platform designed to help small business owners tackle the complexities of marketing. Paige shares how her experience moving from running her own business to in-house leadership roles gave her unique insights into the challenges entrepreneurs face and how Margo helps solve them through guided marketing plans and access to expert resources. We dive into how Paige balances the demands of being an executive, a founder, and a mother, sharing her strategies for prioritizing what matters in the current season of her life. Paige offers valuable reflections on staying grounded, navigating societal expectations, and raising children while pursuing ambitious goals. She also speaks candidly about the importance of choosing work environments that align with your values and allow space for personal and professional growth. This episode is filled with practical advice for anyone navigating the intersection of career, creativity, and caregiving. Whether you're building your own business, balancing multiple roles, or redefining success on your own terms, Paige’s story will leave you inspired to embrace the messy but meaningful journey of a portfolio career.