Bad On Paper Podcast

Episode: What's A Portfolio Career?
Hosts: Becca Freeman & Olivia Muenter
Air Date: November 12, 2025

Overview

This episode unpacks the concept of a “portfolio career”—a multifaceted working life made up of multiple roles, revenue streams, and creative pursuits rather than a single-tracked, traditional job. Becca and Olivia discuss their own career evolutions, interview successful women with dynamic, hybrid careers (author and coach Leigh Stein; creative director and writer Ali LaBelle), and offer guidance for anyone seeking a less linear path in the modern job landscape.

Key Segments & Insights

1. Defining the Portfolio Career

[00:23 – 01:20]

• Definition: Becca draws from Wikipedia: a portfolio career "comprises a variety of roles rather than one job at a single organization. It can be a career that combines multiple paid and/or voluntary roles."
• Both hosts are living examples, blending podcasting, writing, influencing, and more—all increasingly common as the job market evolves.

2. Highs & Lows: Personal Updates

[01:30 – 13:43]

Olivia’s Highs

• DIY Retreat: Hosted a successful, self-organized reading & writing retreat in the Catskills for 19 people.
  • “It was actually really lovely because I would walk around the property and the hotel...and I would just find people in these little nooks...to read or write...it was just like exactly what I wanted to create for people.” [02:26]
• Concert Experience: Attended a small, intimate Joshua Burnside (folk musician) concert, which provided unexpected creative inspiration.
  • “Do you ever feel like you need to do something creative that's, like, passive. Like, you need to observe something beautiful or inspiring, but, like, not actually. Right. Like, I didn't have it in me to do any actual creativity this week, but I needed something.” [05:34]

Becca’s Highs

• Post-Election Hope: Sharing optimism after a major election cycle.
  • “I forgot what it feels like to feel hopeful and not absolutely crushed after an election day.” [07:00]
• Reading Olivia’s Book ARC: Finished Olivia’s new novel, "Little One," in one sitting.
  • “I sat my butt on this couch and I finished the book in one sitting because I could not bear to put it down.” [08:33]
• Light Book Edits: Final edits on her own second book were “so light” and allowed for a celebratory, detailed final pass.

Lows

• Olivia: Burnout from six weeks of nonstop work—seeking rest and resetting priorities. She jokes: “instead of saying, I'm so busy, say life is so abundant right now.” [10:30]
• Becca: The literal noise of city construction and truck traffic—"the soundtrack to a lot of my week was the truck backing up, beeping noise” [12:36]—but enjoying some peace.

3. What Does a Portfolio Career Look Like?

[16:37 – 25:14]

Becca’s Current Portfolio

• Podcasting, novel writing, newsletter (Substack), and influencing (affiliate links).
  • “There are times when it's like, oh, I have four different things and I need to do all of them at once. And that can be stressful...But I think I do prefer this.” [19:43]
• Prefers diversity for income and creativity; having just writing as sole focus created pressure and “made myself really miserable.” [18:26]

Olivia’s Path

• Since going freelance in 2019: writing, consulting, influencing, Substack, now books, and podcasting—but always shifting the balance for sustainability and interest.
  • “Mentally, writing books is my priority...even though I have those three things, and I would say they're all more or less like equal in terms of income.” [22:18]

On Building Events & Community

• Olivia’s bookish retreats: Plans to grow slightly, but prioritizes community over scaling into a full-fledged business.

Interview #1: Leigh Stein, Author & Coach

[25:26 – 44:52]

Career Breakdown

• Book coaching and consulting (since 2017), teaching workshops, Substack newsletter (Attention Economy), book income (sporadic), previously running a feminist writing conference.

On Money & Transparency

• “I'm really interested...whenever I follow writers online, I'm like, what do they do to make money? I want to know how everyone makes money.” [25:57]
• Demystifies the myth of the "full-time" author—most combine jobs, freelance, or have partner support.

Income Pie & Time Management

• Book coaching: most reliable;
• Freelance writing: rare, not stable or suited for her;
• Substack: stable, better than “churning out one article a year”;
• “I track by hand in a paper calendar. I track hours I spend on everything that I'm doing and at the end of the month I tally it all... I can see how much I'm earning per hour for each activity.” [31:15]
• Writing books often gives a surprisingly reasonable hourly rate if you sell them.

On Preference for Portfolio Careers

• Sets flexible schedules; prefers self-direction over a conventional boss:
  • “I'd rather work seven days a week for myself than work 40 hours a week in a cubicle for someone else.” [35:22]
• Full-time writing is “always a fantasy,” but in reality, creative hours are limited (cites “Deep Work” and 2–4 hours/day capacity) [37:21, 38:14].

Advice for Aspiring Portfolio-Career Builders

• Solve a unique problem; offer value (her niche: social media for writers, plot structure).
• Learn marketing and build your own audience; “reliability is very valuable right now.”
  • “If you can learn marketing and you can build your own audience, you can market your services directly...and keep a hundred percent of the money.” [39:39]
• Be honest with yourself about needing structure—some might need accountability partners.

Cons of Multifaceted Work

• “Sometimes I think, like my clients are just paying me to be reliable. Like, reliability is very valuable right now.” [42:51]
• Requires self-management and proactivity; not ideal for everyone, but perfect for self-motivated rebels.

Interview #2: Ali LaBelle, Creative Director & Writer

[44:59 – 66:44]

Her Portfolio Career

• Creative studio and consultancy (branding, interiors, hospitality, fashion, beauty)
• Writes a design newsletter (A La Carte, Substack)
• Pasta Girlfriend: Instagram & event series, hosts pasta-themed events

On Fulfillment and Income Balance

• Design consultancy brings the most income, but writing the newsletter is “my favorite thing that I'm doing.” [46:35]
• “It's hard to rank fulfillment...When I'm finishing a design project versus...chipping away at an editorial calendar...there's more immediate satisfaction in writing the newsletter.” [48:36]

Client Work vs. Independent Work

• With her studio: client’s needs dictate the work; with newsletter and events: personal creative vision and control.
  • “I'm the person that approves it. You know, it's like I'm the last stop, and there's something really empowering about that.” [50:18]
  • The long game is about building something self-directed to grow with her.

Do You Ever Want to Focus on Just One Thing?

• Sometimes fantasizes about it, but ultimately likes the mix:
  • “I actually don't think it would be that good for me creatively to only be focused on one thing. And I actually think I'd probably get bored and end up adding a bunch of stuff back in anyways.” [51:57]

Advice for Emerging Creatives

• Pro: Experience in-house first provides resilience and know-how for freelancing/consulting down the line.
• Con: Freelancing rewards independence, consistency, discipline—"I actually, like, don't recommend it for everybody" [53:46]
• You have to weather financial ebbs and flows, trust good months will follow bad; patience pays off.
  • “I had to go through a few seasons of ebbs and flows to prove to myself that after the ebb will come the flow eventually.” [59:26]

Industry Shifts: Gen Z & The Changing Career Path

• Fewer traditional in-house roles; more people forced into portfolio/freelance arrangements.
• Mentorship and ongoing learning are crucial; “Everyone started from zero…at every level, there’s still so much to learn and no one knows everything.” [63:52]
• The benefit of a portfolio career is building an identity and body of work that’s resilient and grows with you.

Notable Quotes:

• “I think the best way to fight those insecurities...is just to stay focused on the things that I'm doing for me that, like, feel creatively fulfilling for me and like a representation of myself. And at the end of the day, like, those are the things you'll take with you into the future.” [66:00]

Additional Takeaways & Memorable Moments

Tracking Time & Value

• Both guests and hosts stress the value of time-tracking—helpful not just for billing but for understanding and appreciating your own labor and growth.

The Myth of the Solitary, Full-time Artist

• Most writers, designers, and creatives are juggling multiple roles, often invisible to the outside observer.

Practical Wisdom on Burnout

• Diversifying creative work alleviates both creative and financial pressure.
  • “I grossly miscalculated being able to live off of my book advances because I was thinking about it in terms of being able to write a book a year, which I've also learned that I cannot do.” [18:14]
• It’s normal to need breaks and to seek inspiration from others' creativity.

Notable Quotes & Timestamps

• On the reality for creative workers:

  • "I want to know how everyone makes money. I love talking about money...it's also true that in the writing world there are certainly many writers who are able to do this career because their partner has the larger salary and the more steady income. And in my household, I am the primary breadwinner." – Leigh Stein [25:57]

• On the impossibility of “full-time writing”:

  • “It put so much pressure on the writing. It mind fucked me so badly about putting financial and commercial pressure on the writing that made it miserable.” – Becca [36:09]
  • "I think all the time about that Cal Newport book, Deep Work...they max out at four hours. Like two to four hours of deep work is all you can do." – Leigh [37:21]

• On the attraction and challenge of independence:

  • "I'd rather work seven days a week for myself than work 40 hours a week in a cubicle for someone else." – Leigh [35:22]
  • “Sometimes I think, like my clients are just paying me to be reliable. Like, reliability is very valuable right now.” – Leigh [42:51]
  • “You just have to hold on and wait and see. And there are so many times along the way...where I was like, I need to go get a job. Like, what am I doing?...And then the next month I’ll, like, book a big job...it becomes easier over time.” – Ali [59:26]

• On embracing creative fluidity:

  • "I actually don't think it would be that good for me creatively to only be focused on one thing. And I actually think I'd probably get bored and end up adding a bunch of stuff back in anyways." – Ali [51:57]

Useful for Listeners Who...

• Wonder about the “real” lives of authors, artists, freelancers, or designers.
• Are considering or already building a portfolio career and want advice or reassurance.
• Want practical strategies for creative time management, income stability, or balancing passion projects.
• Seek inspiration to embrace a multi-hyphenate, self-directed work life.

Resources

Follow & Connect

• Leigh Stein: leighstein.com, Attention Economy Substack, Instagram/TikTok @leighstein
  • Latest novel: If You’re Seeing This, It’s Meant For You
• Ali LaBelle: A La Carte Substack, IG @alilabelle, Studio: @alilabelleco

Related Book Picks

• Little One by Olivia Muenter (out Feb; discussed at [08:57], [77:11])
• Witch by Meg Shafer ([75:15])
• The Good Daughters by Bridget Dale ([78:26])
• The Correspondent by Virginia Evans ([79:54])

Final Takeaway

The modern creative or knowledge worker’s path is rarely linear; a portfolio career offers flexibility, autonomy, and creative sustenance—but also financial unpredictability and the need for self-motivation. For those willing to embrace the unknowns, the rewards can outweigh the risks, as affirmed by all voices in this inspiring episode.