What's A Portfolio Career?

Summary

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Bad On Paper Podcast

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

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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.

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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.

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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.

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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]

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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.

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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]

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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.

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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

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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])

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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.

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Transcript

[A]

Hi, everyone, and welcome to Bad on Paper Podcast. I'm Olivia Mentor.

[B]

And I'm Becca Freeman.

[A]

And today we are talking all about portfolio careers, which is. Well, Becca, do you want to give the definition for what a portfolio career is before we dive into these conversations?

[B]

Oh, I sure can. I pulled it off of Wikipedia. So a portfolio career, according to Wikipedia, 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. So instead of when I was a freelancer, I did one thing and I had multiple clients. This would be kind of cobbling together your career out of multiple different things. And this is how both of us are making our career right now. And I feel like it's becoming more and more common just given where the job market is. And so we have two amazing guests today. One is an author and then one is a creative in a different field that we're talking to about how their careers work.

[A]

It's good to have perspectives from many different careers and not just authors, even though pretty much all authors have portfolio careers, in case you didn't know.

[B]

Well, before we get into career chat, we have some high highs. I want to hear about what's going on.

[A]

Yeah, I mean, there's a lot of highs in the world this week, I. I think, which is refreshing for once. But in my world, I have two highs that I want to talk about. The first is that I successfully, I think, pulled off my first ever completely DIY hosted reading and writing retreat in the catskills. It was three days and two nights. It was almost 20 of us. I think it was 19, including me. And it was exactly how I wanted it to be. The weather was beautiful, the people were lovely. It was so cool just to be around people who share the same interests and especially the same love of reading and writing. And I didn't really get much reading or writing done, both because I was like kind of observing everything and trying to make sure everything was going well. But also I was just very chatty. So I kept just walking from room to room and space to space and talking. But it was actually really lovely because I would walk around the property and the hotel and the different cabins and stuff, and I would just find people in these little nooks that they had found to read or write, like little spots outside or by fireplaces or like in window seats. And it was really, it was just like exactly what I wanted to create for people. And so it was really special for me. And I'm proud of myself for Figuring out how to host it and put it together myself, because I didn't know how to do that a year ago, but I wanted to. So more to come. I've already started planning the next one.

[B]

Well, I've got to tell you that based on Instagram, it looked absolutely dreamy. And it felt so you like. It almost felt. And I was seeing the stories that you were reposting that other people were posting, that people got to kind of like slip into your world, you know, both in terms of your area of the country and all of the beautiful trees and nature, but then also the coziness and the reading and writing. It looks perfect.

[A]

Thank you. It was also really special because there were some people who had met on my past group trips. There's these two women, Marielle and Megan, who came on my first trip, my Vermont trip. And since then, they have gone on, I think, six friend trips together. They have this best friendship. And they were both there and they both messaged me afterwards, and I'm going to cry. And we're saying how I, like, brought them their person, like their best friend that they were meant to find. And it made me so emotional. And it is now, but I don't know.

[B]

It's lovely.

[A]

It's so cool. And so, yes, it was a very high high for me, and I can't wait to do it again.

[B]

That's so lovely.

[A]

Thank you. Okay, so my second high is that last night I went to a concert in Massachusetts, which I was extremely tired from the retreat and from. I've been running around. I was in the city for a day, basically. But I have been really into this musician this year, and his name is Joshua Burnside. I've been listening to him nonstop. He's from Northern Ireland, and it's kind of like folk music. I really love indie folk music. His voice is enchanting. The way he plays guitar. I just. I absolutely love him. On a random whim, I Googled two weeks ago or three weeks ago if he was playing any shows near me. He lives in Belfast, but randomly, he was playing one at this very small venue in Northampton, Massachusetts, which is an hour and a half from me. And so last night, Jake and I went there, and it was. I think there were maybe Max, 75 people in this room. I mean, oh, how special. Oh, maybe fewer. So small and just really, really cool and so incredibly talented. And I just. I think it's exactly what I needed because I'm feeling a little bit burnt out. And I. 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. Do you know what I mean? Yeah.

[B]

Being around other people's creativity can be energizing. Or hearing people speak about their creativity. Like, I often feel really energized if I go to an author talk event, even though it has absolutely nothing to do with me.

[A]

Exactly. Yes. And so it was energizing, like you said, to just be in a room with someone who I admire so much and I, like, get so much out of his music. And to know that he's from this city in Northern Ireland and somehow his music has brought him to this random town in Massachusetts. And I drove there three hours round trip to listen. And I don't know, it was just something about. It was really special. And I just kept having this thought during the concert of, like, this is, like, what it means to be a human, just to watch other people just be creative in front of strangers and be brave in that way. And anyway, I highly suggest anyone who is into folk music, indie folk music, to check him out because I just. I don't know how he's not more well known. But anyway, we'll link some stuff in the show notes if you're curious.

[B]

Yeah, I haven't heard of him. I'm excited to check him out.

[A]

He has so many good songs. I don't even know where to start. But anyway, tell me your highs. We have a lot of highs. To get to this episode, I have three highs.

[B]

My first one after the election last week. I am feeling so energized, feeling so hopeful. You know, both in New York City, who elected a new mayor, and then also all around the country, a lot of seats flipping. California's Prop 50 passed. Like, I am just feeling so hopeful, and I forgot what it feels like to feel hopeful and not absolutely crushed after an election day.

[A]

So.

[B]

Oh, my gosh, I feel like it has so seeped into every nook and cranny of my life in a way that I didn't realize that I was holding on so deeply to negativity, fear, anxiety, et cetera.

[A]

Yes, I am also feeling really energized and really happy for New York City, but also also Virginia, Virginia's new governor, and also just the country. I think it's a. We needed this. We really did.

[B]

I'm feeling so good. Second thing, I got the package, I got the mail. I have been waiting For I got an ARC of your book, Little One, which comes out in February. It was in the most gorgeous Brandon Mailer and it's a soft cover, you know, pre publication version of the book, but it still looks so beautiful. And then, Olivia, I had a top recent reading experience, just absolutely scarfing it down. I sat down on my couch that night and I was like, I want to start it right away. I'm just going to read 50 pages. Olivia, I sat my butt on this couch and I finished the book in one sitting because I could not bear to put it down. Oh my gosh. We can talk more about it in the reading section at the end. But I am so proud of you. I am so excited for our listeners. For anyone who gets to read this, oh my gosh, it's so good.

[A]

Thank you so much. That means a ton to me. And it's so weird that it's finally out in the world and that you are reading and everyone is in some way, even if it's not out yet. But thank you so much. It's very, very nice of you.

[B]

It's not nice of me. It's true. Thank you. Because you gave me such a great reading experience, which I value so highly. So that is my second thing. My third thing is that I got my final round of edits on my second book. They came in Thursday and I spent this morning going through them and they are so light, I hesitate to even use this word for fear. It bites me in the butt, but it feels easy. I am so excited. I'm so excited to get back into this book, knock off these edits. It feels really good that they're light, that my editor thinks that this book is in good shape and is excited about the work that I've put into it. And then I'm really excited to kind of go back through with a fine tooth comb and get to do my final pass on the sentences and just really focus on tightening and beautifying everything without having to worry about, you know, higher order edit concerns of like this character or this scene isn't working and just really sink into the most granular level. I'm so excited.

[A]

What a nice way to just round out the year. This is so amazing and I'm so happy for you.

[B]

Thank you. What about on the low side?

[A]

My low is, you know, I saw this video from Hipha, friend of the podcast the other day and she was saying, instead of saying, I'm so busy, say life is so abundant right now. So maybe I will say that life has been Very abundant. And I need, I think, a couple days off between the retreat and book three stuff. I have worked every single weekend day for six weeks now, which is very unlike me. It's all stuff I love to do. So I thought, oh, this won't, this won't affect me. But I have found myself post retreat feeling incredibly burnt out. So I just need a couple days off. I need to reset. I need to re energize. I need to sleep. I slept for 12 hours last night. I had a dream I need to share because I think that you and the listeners will appreciate that this is the most Olivia dream that one can imagine. I was in a thrift store. I had gone back to the thrift store to look for an oil painting that I absolutely loved. But for some reason I left behind, I couldn't find it. So then I. I was getting a bunch of taper candles instead. I had an armful of half used taper candles. And I get to the checkout and I see someone in line so far.

[B]

I'm like, was this a dream or was this a sleepwalking real life experience?

[A]

I get to the. I get to the checkout line and I see there's a woman in line holding the oil painting. And I'm like, damn it, who took this for me? And the woman who took it was Jenna Bush Hager.

[B]

Of course she did. She's always scouring those upstate thrift shops for oil paintings.

[A]

You don't need to thrift. You don't need to thrift. Go buy it. No, no, I'm just kidding. So I just had to laugh when I woke up because I was like, okay, I think this is a sign I'm kind of getting back to my fully rested self because this is kind of where my brain lives normally. It's like Jenna's book club. Books, candles, thrifted oil paintings. So anyway, I am resetting. I am feeling refreshed and more like myself today. But I was. It was rough there for a while.

[B]

Oh, I'm glad.

[A]

Well, what's your low?

[B]

My low is just that it has been a busy week on my corner for construction. And it is not so much the construction that is the problem. The problem is that because they were doing construction on the street, trucks would then try to turn onto the street and then get stuck. And I feel like the soundtrack to a lot of my week was the truck backing up, beeping noise, and. Or other people honking at the trucks that were stuck. It was a not great sonic week here at my apartment.

[A]

I hate the back backing up beeping sound. It's really not good.

[B]

Terrible. But I am happy to report that either they're taking a three day weekend or they are done. So no, no construction today.

[A]

God bless. Well I hope they don't come back.

[B]

I hope so too. Let's take an ad break and then let's get into today's topic.

[A]

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[B]

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[A]

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[B]

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[A]

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[B]

Olivia, I am very excited for these two conversations that we have teed up, but I think as always, if we're asking people to show us theirs, it's only fair that we show people ours. That phrase didn't quite work in the plural the way that I thought it would.

[A]

Wow.

[C]

Okay, less and less.

[A]

Let's get into it. Let's. I don't know, I was gonna say let's undress, but that really is even weirder.

[C]

That's even weirder.

[B]

Hr hr.

[C]

So sorry.

[A]

Okay, well, let's start with you and your portfolio career.

[B]

Yeah, I don't know if I would have claimed this term up until maybe even this year. I've always had the podcast and then, you know, I was doing freelance writing. I had the podcast and writing novels. But I don't know, it wasn't until I had three or four things that I started to think of it as more of a portfolio career. But I guess right now if we look at the different things that I do, I have the podcast, I have novel writing, I have the newsletter. New this year, I have influencing. Using kind of sharing affiliate links on Instagram and in my newsletter has become a revenue stream for me. But I'm definitely identifying more with this term where there's kind of multiple things contributing, especially to my income, as opposed to having one main thing, which I feel like I've been more accustomed to in the past.

[A]

Do you prefer your career this way to just working on one thing? Do you wish that you were just doing just writing a novel, for example, and none of the other stuff existed?

[B]

That's a hard question. I think there are definitely days when I'm tempted to say yes, but I also recognize that I kind of Tried that last year, and I very much made myself miserable because it put so much financial pressure. It put so much pressure on needing the novel to be so perfect and needing it to be commercially successful in order to keep doing this, in order to keep paying my bills. I definitely was so hard on myself and I made myself really miserable doing that. And so this year, one of my goals that I had this year was to figure out my income situation and diversify my income so that books are a part of it, but it's not all of it. And also, I think I've said this before, but 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. So I think that this is much more sustainable and it asks much less of my creativity and puts less pressure on the books. But I think one of the downsides of this type of career is that it's not like when you work for a company and everyone is aligned on priorities. 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. You know, like, we need to put up. We don't need to, but, like, it's important to me to put out a podcast episode every week. It's important to me to stick to my newsletter schedule. And so, yeah, there's definitely times where I'm like, oh, man, it would be so much easier if I only had to focus on one thing. But I think. I think I do prefer this also, I've said this before that I do think I get especially out of the podcast. The rest of the aspects of my career are so introverted that I do think that the podcast is really important to me as an outlet to have an aspect of my career that's more interactive and allows me to gab.

[A]

Are there ways that you'd like to see the portfolio career evolve?

[B]

I don't think so. I'm definitely not thinking about adding on any other. Any other assets if we're continuing the portfolio analogy. No, I feel pretty happy with it right now. Maybe that'll change because of external circumstances or because I enjoy spending my time in one place more than the other. But right now, I feel pretty satisfied this year career wise in a way that I don't think was true last year. What about you? Take me through how you view your career.

[A]

Yeah, I guess I've had a portfolio career of some kind since I went freelance, which was in 2019. So it's going on almost seven years, which is you're a veteran, almost double the time that I worked as an editor, which is kind of wild to think about. So I've always had multiple streams of income because I found out pretty quickly that, at least for me, it wasn't even remotely realistic to just do freelance writing. So I've done consulting, I've done obviously, freelance writing. I've done influencing, I've done sub stack. Now writing books, podcast, a lot of different things. And it feels very normal to me to have like the income pie and also to shift things around based on what's working, what's not working, what I want to prioritize.

[B]

It feels to me like you derive so much pleasure from the writing process, though. Do you aspire to be able to have that be a hundred percent of your career one day, or do you still think you would keep other revenue streams or aspects of your career even if you were able to support yourself purely off of books?

[A]

I definitely have days where I wish I just had writing books to focus on. But if I'm honest, I think that I like having different spaces to be creative in different ways. I love podcasting. I can't imagine a world in which I give it up. I don't think I can ever see myself writing a book a year, which to me is like the only version of writing a book where, like, it wouldn't be even remotely feasible for me to also be doing multiple things. And so I think I'll always have multiple things. I mean, I think the way I think about it right now is right now, my pie is substack podcast book writing. That's it. And then if you squint, if you zoom, zoom, zoom far in, maybe there will be like the tiniest.001% from planning these group trips. But, you know, that's still, like, in the early stages. Maybe one day it can be a little bit more. But the way I think about it is, even though I have those three things, and I would say they're all more or less like equal in terms of income, mentally writing books is my priority. So if something has to shift, like it's. It's really books, then the podcast, and then my substack unfortunately comes in third, I still do try to produce quality content, but if there's a week where I am too busy to put out a post, then that's what it is. I'm always gonna prioritize the other two things ahead of it.

[B]

Do you aspire to, and I don't want to discount the connection and experience you have, but do you aspire to have the retreats be kind of a more that you don't have to zoom as far in to see it as a contributor to your income or is it kind of just a for fun thing? Because you also had the book fair that you did last year, which is different than the retreat, but it was still like a community building thing and at least as far as I understand it, you did that of like the goodness of your heart for your local and book communities.

[A]

Yes. I mean, I think for me, I would like to, in a dream world, be planning two bookish trips a year and if I could make a little bit of money from them, that's fine for me. To me it's more of like the community part of my career and the connection thing than I. I don't want to turn it into a business. I don't want to turn it into like there's 10, 15, 20 trips a year. I have no interest in that. I want these to be trips that I would want to go on and that I will go on.

[B]

That would be hard too because you can't scale yourself, you know.

[A]

Right, exactly.

[B]

And you're such a critical part of these trips.

[A]

The idea is that they would enjoy them without me and I'm sure they would, but like I just enjoy planning them so much, you know, so to me it would be like if I could make them a little bit profitable. So it's like a bonus and I'm more than breaking even every time, then that would to me would be a win. I have no interest in making it like a business.

[B]

Yeah, you know, well, why don't we hear from a couple of other people about how they are thinking of their portfolio careers.

[A]

We are so excited to have Leigh with us today. Leigh Stein is the author of six books, including the best selling gothic mystery, if you're seeing this, it's meant for you. And the critically acclaimed satire Self Care. She writes the Attention Economy newsletter on Substack. Welcome Lee.

[D]

I'm so happy to be here.

[B]

Thank you. Well, I feel like we have to start it because when I emailed you to invite you on this podcast, you were like, I have thoughts. So instead of asking you questions, you're going to start, I got to, I want to hear what's on your mind portfolio career wise.

[D]

Oh, I just get the most like interesting questions. Like I taught a social media workshop for writers and at the end they Were like, do you have a job? And I just thought like, do I have a job? Like, to me I'm like, isn't it so obvious that how I make money? Like, I feel like the ways I make money are public. Like I'm promoting the ways in which I make money. But I guess to some people it's like invisible. And I guess I'm really interested. This is just something I'm like personally curious and interested in. Like whenever I follow writers online, I'm like, what do they do to make money? I want to know how everyone makes money. I love talking about money, I love thinking about money, and I want to know. 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.

[B]

Oh, fascinating. I'm so curious to hear more about all of this. But I, I feel like very naive to say, but I feel like before I became an author, I don't think I realized how many authors have portfolio careers or doing things outside of, you know, whether that's having a full time job or having a bunch of other side hustles or you know, working in academia and being paid to do their writing work through grants or something like that. I don't think I realized that because before I started writing, I feel like a lot of the authors that I followed on Instagram were huge authors. You know, it was Ellen Hildebrands and Liz Gilberts and Taylor Jenkins Reid and it was people who do do this full time. And so I don't think I necessarily realized that the mid list work a day author had in most cases either has family money or a spouse who is able to pay the bills or has one to many jobs. So yeah, that's something that feels very obvious now, but I didn't realize until recently.

[D]

I wonder if it also is like a kind of category difference because I am a literary novelist and a poet, so I'm not a commercial fiction author. So when I was coming up as an artist, as a poet, like it never occurred to me that I would make a full time living as a poet. Like that thought never flashed across my little brain. And so I just knew I'd have to work if I wanted to be a writer. And in my world, the literary writers are most often like creative writing MFA professors. Like that's a very common track that that's your study income so that you can write literary fiction like once every 10 years.

[A]

Can you tell people what are the different ways that you put together your career right now? Like, what are the different facets? What are the different sections of the sort of income pie chart?

[B]

Yes.

[D]

So since 2017, I've had my own book coaching business. And I started that business after burning out running a feminist writing conference. I went into debt running this feminist writing conference I was making at my highest earning running the feminist writing conference. I made $12,500 in a year. So I had multiple side gigs in order to be able to do this. I went into credit card debt. I burned out, I resigned. And I asked myself, like, what are people always asking me for advice about? And writers were always coming to me to ask me book publishing advice. Because there's a lot of information about writing. You can go to school to become a writer. But book publishing is very mysterious. And I like the business of book publishing. I learning that. So I realized, like, oh, I could actually charge money for this service of coaching people, helping them publish books. And at the beginning when I started my business, I charged $250 a month. That got you four coaching calls a month with me. And when this worked, it's a deal.

[B]

Bargain of the century.

[D]

And when it worked and people, like, wanted to book this service with me, I was like, this is incredible. It was just like, it felt like such a win. So that's how I started. And as of today, I have a stream of income from that coaching. So I have some clients that are just hiring me personally, one on one. So I do one on one kind of consulting and coaching and editing. I also teach classes, so I earn income from that. I earn income from my Substack newsletter and I earn income as a writer. But my writing income is the most uncontrollable and variable. You know, years can go by with me earning $0 as a writer. I used to do more freelance writing and freelance pitching. And I'm not fast. I'm not good at it. Like, I would write like one freelance.

[C]

Piece a year, you know, just like.

[D]

That'S not a job. Like, that's just like a supplemental thing. So for me, making money on something like Substack, where I'm publishing a newsletter every week and I'm providing certain kind of value to my paid subscribers that to me is much easier and more stable source of income than freelance pitching or freelance writing. So all of my writing income at this point comes from books. And I've written and sold six books over the course of 15 years.

[B]

How do you think about how the different facets of your career contribute in terms of like income versus time versus the fulfillment you derive. Like, are they all equal pieces of the pie or do they kind of, you know, is one of them like, oh, I'm doing this thing so that I can fund writing books, which is less consistent or brings in less money, but is like my true passion. How do you think about the different contributors to your career?

[D]

That's a really good question. I would say I at this point, like enjoy everything that I'm doing equally. But it's absolutely true that I have kind of designed a business that is flexible so that when I am writing a book, I can tell myself, like, I'm not taking calls before 1pm because I'm going to write every morning. Like, I have the luxury of designing my schedule now, which is perfect for writing or perfect for my schedule? My brain as a writer, I know that I like to write in the mornings and so I can schedule my paying consulting work around that. I am like a meticulous time tracker. And so 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 and in a spreadsheet I can see how much I'm earning per hour for each activity.

[B]

Oh, wow, that is fascinating and terrifying. I do not want to know what I'm making on an hourly basis writing books.

[D]

But you know what? There's all this. Every so often something will go viral on the Internet. Like writing a book is like less than minimum wage. Complaining about how much labor it is and you get so little money in return. I can actually see how many hours did it take me to write and revise my novel. I know how much my advance was. I think it works out to like $100 an hour to write a no. Which is not minimum wage.

[B]

Interesting. Did you see that Delia Kai wrote a series on writing a book on her newsletter? And in it she also has a very meticulous time tracking spreadsheet that she uses. And I'm kind of intrigued by doing that. Not to calculate my hourly take home pay from writing, but just to understand how many hours does it actually take to write a book for me. And I'm sure it's different for every book and for every author, but I am kind of interested in trying to track more granularly for book three to kind of understand and also understanding, you know, how many hours does it take to write a first draft? How many hours does it take to write A second or third draft just to understand that. Because I feel like it's such a long term project that I kind of lose the thread a little bit. And you're relying on memory, which isn't necessarily super accurate.

[D]

I love tracking. And it's also like a way to get around the excuse, like, well, I don't have time. How could I write a book? I don't have time to write a book. But then when I look at it, I'm like, okay, 20 hours a month over 30 days. You know, like, I track writing versus career. I separate those two things out. So time that I'm spending promoting my book, doing a podcast interview like this, this gets counted differently.

[B]

Oh, we're going in the spreadsheet.

[D]

Oh, you're going in the spreadsheet. And I also, like, can look at the end of the month and be like, wow, I felt so tired this month. And it's like, wow, my. My monthly hours are way up this month. Or, you know, I was doing a lot more of this than that. Or I can set a goal for myself. Like, next month I'm gonna do more hours in this bucket. So it really works for me.

[A]

That's interesting. I kind of do something a little bit similar. I have a very basic spreadsheet and have for years where for a long time it was freelance writing assignments. And it's weird, like, the list got smaller as I wasn't doing like 150 SEO articles every month trying to pay the bills and I was doing bigger things. But now with book stuff, I have started putting things on there that aren't necessarily paid, like interviews or like pitching essays in relation to the book. All of that gets put in there. And like, there's no like, actual number in the money column. But it still makes me realize that, like, okay, this is actually part of it too, even if it's not like a. Like, there's no hourly rate necessarily.

[B]

Yeah.

[D]

But it's like a way to visualize or quantify all the labor you're doing. Like, it's like I want to keep some kind of record of all I know how hard I work. And I just find it satisfying to be able to see it in some way, to count it in some way, to know that it counts.

[A]

I love that.

[B]

How do you feel about having a portfolio career? Do you like it this way or do you have a deep seated dream that one day you will not have to do all of these other things and can just write books?

[D]

That's a great question. Compared to working full time I've had one 9 to 5 job. It was at the New Yorker for one year. I was the assistant to the COVID editor. I couldn't wait to get out of there. Like, I hated being in a cubicle. I hated having to be somewhere even if there was nothing to do. So my lifestyle now, it's like, I'd rather work seven days a week for myself than work 40 hours a week in a cubicle for someone else. And, like, have the busyness and the slowness be determined by someone else. So compared to that, I'm very happy. It is always a fantasy to write full time, but what would that even. What would it even look like to write full time? Because it's almost like on the outside it looks like you, Becca, write full time, but you doing this and you're doing substack. Like, it's not full time writing.

[B]

No, it's not. And I think in 2023, after I sold my book, I thought that I would write full time. And I wasn't doing substack really yet. I was just using it as an author newsletter and everything was free. I was not making any money from it. And I had the podcast and I thought that I could write full time. I think that was. We talked about that in the upfront, but like, it was a misguided assumption based on writing a book a year, which I thought was realistic because other people are doing it. And I realized, oh, no, I can't do that. And 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. Like, it wasn't like, oh, I wrote my first book in, you know, kind of mostly 10 to noon, two hour chunks. And it was like, okay, if I now have eight hours instead of two hours, it's like, I don't know that I'm gonna get much more than two hours of actual creative writing done. I can write newsletters. I can do some of the more business or marketing or promotional aspects of my author career outside of that. But it's like, it's not like I can 4x my writing output.

[D]

I think all the time about that Cal Newport book, Deep Work, where they, like, study the working habits of geniuses and they max out at four hours. Like two to four hours of deep work is all you can do. And then your brain is like, we gotta do something else. So writing eight hours a day, I don't know. I don't know anyone actually who writes eight hours a day.

[B]

I hear stories about People who go into really obsessive fugue states writing their books, like Rebecca Yarros is one who will. It sounds like, you know, write a first draft in three weeks or something where it's like, couldn't be me, Couldn't be me, Couldn't be me. And I think I thought that's how I would feel if I had the time. And it is. It is not.

[D]

Well, Cheryl strayed too. Like, she talked about, like, riding wild, and she had young kids and she would just like, check herself into a hotel for two days away from her kids and just like, binge.

[B]

Right.

[D]

But I'm more of the can we do it two hours a day, most days a week kind of approach. That's what works for me. And then I just run out of. I like, run out of juice.

[B]

Yeah, yeah. And then even if I keep writing, sometimes, you know, sometimes you hit a chapter and you're like, I can see this so clearly and I'm just going to get it down while I have it. But, like, more often than not, you, like, keep writing longer and you go back to it the next day and you're like, I know this is English, but none of this is good or makes sense.

[A]

It's true. I also, I love what you said in the beginning about, like, the difference between having a partner with a stable career. Because I always try to tell people when I talk to them, like when I went from a full time, like, editorial 9 to 5 to freelance, like, part of the reason I could take that risk is because I have a partner who has a stable career. And that's not to say that he's paying my bills, but that if something goes horribly wrong, I'm not out on, you know, out at sea on my own. And I think that's. It's a really important detail to be transparent about when talking to people because it does make a difference. Because all of these portfolio careers, freelance writing, it requires a great deal of risk.

[D]

Yeah.

[A]

And it's. It's different depending on your circumstances, how much risk you're taking on. So. I love that you said that. Is there anything else you would tell people who are, who are like, I'm considering, you know, building a portfolio career of some kind of.

[D]

Oh, well, first I would just say, to say a little bit more about my story, my husband was the one. He was my boyfriend at the time, but he was the one with the stable career. When I was running my conference, he was the one paying the mortgage on the apartment where we lived. And so that allowed me to take a lot of risks with this crazy. I started a conference based on a private Facebook group of 40,000 people. It was insane. But because he works in tech and media, he's been the victim of a series of layoffs over the course of our whole career. And it's just ended up this way where now I'm the one with the stable business. So it's just an interesting flip, but advice I would give to people. Like, I think if you can answer the question, like, what problem could you solve for someone? So like starting a business based on what problem you're uniquely good at solving, instead of thinking like, wow, I would really love to fill in the blank. It's like, what do people need that you are uniquely good at? Because in my case, like there are a lot of places you can study writing. There are a lot of writing classes. But I found a niche for myself teaching social media to writers because that's what they really have problem with. That's where they're suffering. They know they're supposed to be on social media, but they think like they just have to hold up their book and keep self promoting and then that makes them feel disgusting. And so I'm trying to help them become content creators. I figured that out as a niche. Also plot structure. I realized a lot of writers were taking writing classes and they were never being taught plot structure. And so I figured out how to teach a class about that. So that's how I found a way to make it work for myself. I also think with someone with a business like mine where you're providing services, you have to learn marketing. Because I started teaching writing for Catapult, which has since gone, would no longer exist anymore, but I would teach writing classes through Catapult. And you split the revenue, I think 60, 40 or 50, 50, I can't remember, but I would be getting half the money. But if you can learn marketing and you can build your own audience, you can market your services directly to your own audiences and keep a hundred percent of the money. So that's a huge thing that I've learned. And people even approach me and they're like, lee, do you want to teach a class? And here's what would be the split. And it's like, but why would I share at this point? Because I have 14,000 substack subscribers that I can market to. So it's worth it to learn marketing. And it's funny because as a child, I'm an oldest sister, I love to play make believe, like, but it's always like the darkest. Like, let's pretend we're sinking on the Titanic. Like, let's pretend we're orphans. I love to play school where I was always the teacher. I wouldn't let anyone else be the teacher. And I love to play, like, have a business. And like, it's just like, that's what I've grown up to do. Like, I've been doing, like, to Becca's question about, you know, whether my life would be different if I could make a full time living as a writer. Like, I'm actually doing all the things I've loved to do since I was a child.

[B]

What about on the con side? If somebody was thinking about going into this, like, what would you say are the biggest negatives of having a multifaceted career? Because I do think that sometimes people idealize it in a way and they're just like, do you, do you just like watch TV in the middle of the day or, you know, and it's true. Like, I do go grocery shopping in the middle of the day for the most part, you know, I am able to just like be like, hey, nothing's clicking right now. I'm gonna go for a walk.

[D]

That's literally what my mother in law said to me. She was like, I don't know how you work from home without watching TV all day. And I was like, that never even occurred to me to watch TV in the day.

[C]

Like.

[D]

But yeah, you have to be. I'm accountable to myself. I'm accountable to my clients, but if I didn't meet deadlines for them, I wouldn't get any more clients. I would much rather be accountable to myself than have a supervisor. I do not want to have a supervisor. I'm like anti authority by nature. I'm a rebel by nature. And so it suits my personality. But yeah, like you, I do stuff in the middle of the day. I have some days today, this is my fifth call of the day. I have other days where I don't have any calls. I love that flexibility. But I never miss deadlines. I'm very reliable. Sometimes I think, like my clients are just paying me to be reliable. Like, reliability is very valuable right now. Having someone that you can rely upon and trust, that's a service that you provide. So if you know that you're someone that needs to be managed or someone that needs accountability, you could always start a portfolio career and have some kind of a built in accountability group. Like maybe you team up with two or three other small business owners in your niche and you have weekly or monthly Checking calls that could be really helpful. Like when a young therapist, you know, starts by having supervision so that they don't have to solve every problem on on their own.

[A]

That's very good advice. Lots to think about. I could talk about this stuff for ages. But can you tell everyone where they can find you in case they would maybe want to work with you or follow you, read your books, all those things?

[D]

Sure. My website is my name L E I G H S t e I n.com and I write a substack newsletter called Attention Economy. And I am also on Instagram and TikTok.

[B]

And how did you not include your most recent novel in that? Give us the quick 2 minute pitch for your newest book.

[D]

Okay. My newest novel is about a 39 year old aging millennial who can no longer find work in the media industry. And a man she hasn't spoken to in 20 years offers her a job opportunity managing his TikTok hype house. And she arrives. But one of the influencers from the Hype house has gone missing.

[B]

And this is. If you're seeing this, it's meant for you and it is out now and you can get it wherever books are sold. This has been great. Leigh, thank you so much for sharing, so much wisdom.

[D]

My pleasure. Thank you for having me.

[B]

We are so excited to have Ali LaBelle with us today who is a creative director and writer in Los Angeles. Her creative studio, Ali LaBelle Creative, is a branding and design consultancy for focused on building brands across interiors, hospitality, fashion and beauty spaces. She's the writer behind the A La Carte substack, a newsletter about design and creativity in all its forms and runs the Instagram and event series Pasta Girlfriend. Welcome, Allie. I'm so excited to have you.

[C]

Thanks, guys. It's so good to see you, Becca, again and good to see you for the first time, Olivia. I'm obviously a huge fan, so thanks for having me.

[A]

Ditto. Thanks for being here.

[B]

I was saying before we started recording that when I was thinking of people I know who have multifaceted careers, you were one of the first people that came to mind. Do you identify with the term portfolio career?

[C]

No, I haven't heard that phrase before until you said it in your email. But yes, totally. I think that I probably identify with that in a couple of ways in that a portfolio is a really important part of me getting work and also that I have a portfolio of jobs that I'm always working towards. And so, yeah, definitely, that definitely applies.

[A]

I don't even know how many years that I have followed your career from afar. But to be honest, I'm aware that you do a lot of different things and all of them seem extremely cool. But could I name every single one of them? Probably not. So can you tell both of you, me and the listeners, what are the different aspects of your career and income pie?

[C]

Absolutely. And you're not the only person that's confused. My family's confused. I'm confused all the time. So the bulk of what I do is through my design studio and consultancy. I'm a creative director and I facilitate rebrands for brands in a lot of different spaces. All the different ones that Becca named earlier, my background is in design and creative direction. And so that applies to. To, you know, I do a lot of websites, do a lot of print work, you know, anything that kind of falls into the graphic design category. But increasingly over the last couple of years, since I started my substack a la carte, that's really grown into something that it doesn't necessarily compare to the piece of the income pie that the design studio does, but it's become a bigger and bigger part of it over the years. It's also become my favorite thing that I'm doing. And so I'm always trying to get that piece of the pie to grow a little bit more, but that's a big part of it. And I do some partnerships and product collaborations through that arm of everything. And then pasta girlfriend, like Becca was saying, is this like Instagram account, slash, event series, slash, a bunch of other things that I'm always working on that I kind of put up, I pick up and put it down in between other projects. And I would say that's the smallest piece of the pie and almost invisible piece of the pie, but it's something I really enjoy doing and it's a place I get to like, exercise my love of hosting and cooking and all of those things. And so it's on the list of 1099. I get tax season. And so those are kind of the three big categories of things I'm working on.

[B]

And how does it kind of work for you in your head when you think about like the income contribution, the time commitment and the fulfillment that you're getting from them? Because it sounds like from what you just said, maybe the design studio is the biggest piece income wise, but it sounds like substack and what you're doing there is maybe where you're getting more fulfillment. Like how do you think about the balance that it's not necessarily three equal sized pieces of pie?

[C]

Yeah, it's hard to rank fulfillment for me because it's a different type of fulfilling. When I'm finishing a design project versus I'm kind of like, chipping away at an editorial calendar on. On a la carte. And I think there's more immediate satisfaction in writing the newsletter because I write it, I design it, I put it out there, I get a reaction. It's exciting. I am talking to people about it, and then I move on. Where with design work, I just finished a project that I've been working on for two years and, like, couldn't talk about it with anybody or. And no one cared, you know, so it's like. But I'm so proud of it, and it's so fulfilling in its own way. And so I think as it pertains to time, it's pretty consistent amount of time that I'm putting into a la carte. I would say I'm probably spending at least one full workday a week on a la carte, probably a little more than that. But some weeks with the studio, I'm like, on email here and there, and that's pretty much it. Some weeks I'm like, doing a huge deep dive and writing a creative brief, and that takes a lot of time. It really just depends. And so there's not a perfect proportionate way for me to look at my income versus the time I'm spending because it fluctuates so much.

[B]

Well, I also imagine, and I'm saying this from my own experience too, having done client work in the past, that there's a difference in terms of, you know, with the design studio, you're working for a client versus with pasta, girlfriend, or a la carte. It's like an expression of you. You're building your own brand. It's. I don't know, maybe feels higher stakes in some ways or. I don't know, does that ring true for you at all?

[C]

It feels higher stakes, but also, like, so much more freeing and so much more creatively satisfying. I think one of the things I love about doing my own projects is that while I'm, like, collaborating with my designers or everyone else who's part of it, it's like 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. And when I'm. I'm sure you can relate. When you're in the middle of client work and you're like, getting your eighth round of notes back on something, it's like, okay, like, at a certain point, you're like, I no longer am deriving any pride from this project. So, yeah, it's satisfying in a different way. And I think that, like, I'm hoping that I'll have a big, long career for a long time and that I have a lot of life left to live. And so working on things for myself feels like it's playing the long game. Like, I'm working on something that, like, will evolve and change as I do. And what might be creatively fulfilling today might be different next year, where, you know, working on client work is like, I'm really just trying to get the project done and do a good job and get paid for it and move.

[A]

Along, speaking for myself. But also, I would kind of guess that most people who have these types of careers, like us, that are a bunch of different things that work together to form a full picture, have days where we fantasize about only doing one of the things and just thinking about how great that would be. Even if in my case, for example, I kind of know deep down I like having a little bit of everything. Do you resonate with that? Do you ever wish it was just one thing, or does the mix of everything really work for you?

[C]

You know, it's hard. I think, like, my identity is really wrapped up in my design work, and I feel like some of my validity as a writer around creativity comes from the fact that I own a studio and that I'm a working designer. And so, yes, like, in a workload sense and even just, like, in a brain space sense, there are days when I'm like, God, I wish I just wrote this newsletter and could, like, make bank off of it and just be, like, golden and that's it. But 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. And so I think I try to embrace it and just, you know, sometimes it's crazy. Sometimes I get to focus on just one thing or another and that part of it. For how much of a person? I'm, like, ultra consistent and love planning, and I'm, like, not great about surprises. Like, I'm. I'm a pretty, like, regimented person. All that said, like, the fact that I sit down every day and that every day looks different is really fulfilling for me. And so, yeah, I guess I don't find myself wishing all that often that I was only doing one Thing.

[B]

Well, that's good. That means you've constructed the career that you should be in, hopefully. I'm sure you get hit up for advice all the time. Like people who want to pick your brain and if somebody's listening who is maybe in school or is working a full time corporate job and they're looking at your career and they're saying like, hey, that looks good, Cool. I want that. What is your, like, go to advice for people and then, like, what would you say is the biggest pro and the biggest con of having kind of like a multifaceted career like this?

[C]

I think the best thing I did for my career was that I worked in house for a long time. I worked at a company called Bando for eight years. I was the creative director there. And even though, like, this was all pre pandemic, pre pandemic industry looked so different than it does today, like, I was growing kind of increasingly antsier and less happy at my job over the course of those eight years. But I really felt like my only opportunity for a next step was to get a job somewhere else. I didn't, like, freelance, didn't feel like it was as possible pre pandemic. And the pandemic, like, tossed all the cards up in the air and was like, we don't have in house creative teams anymore. People are making up their jobs, they're doing a million different things. And so at the end of 2020, I was like, I'm going to take this opportunity and this is when I'm just going to go try this. Everyone else is getting laid off or is starting something new. This would be the time to explore. And so I'm really grateful for the experience I had working in house because I think it taught me so much about branding from the inside out. Like, you just learn so much about merchandising and partnerships and, like, that's all really valuable stuff that I bring to my clients. But if you're someone who's working in house and you're like, oh, I wish I could just work for myself, like, start compiling everything that you've learned and start thinking about, like, what is your experience at that place that is different than someone who's been freelancing all along or who maybe works for a design studio and, like, is only ever on the client side, like, it's a really valuable perspective to have. And so I wish I had spent more time kind of like being organized about here's all the things that I do and here's all the things I've been learning along the way, because it took me a couple years after I went freelance to say, okay, this is what I'm actually doing. Like, these are my services. This is what my studio does. I took a couple of years to like, art, direct photo shoots and do random stuff all the time just to make money and kind of get myself going. I would also say that, like, freelance or owning your own business is like, so rewarding and the pros are so long. For me, they way outweigh the cons. But like, I do think you have to be like, truthful with yourself about whether you have like, the right personality to work alone and to manage everything. I think that you have to be super organized and curious and proactive and disciplined and like, we're not all of those things all the time. But like, those are the biggest struggles for people is that they feel like constantly like they're doggy paddling and just trying to stay above water or that work is slow and they don't know what to do in those in between times. And you just have to, like, have fortitude and be like, I'm trusting that something's coming along. I'm going to use the time in between slow times to like, get creative and do a passion project or try something new or go chase new work or whatever it is. Like, you just have to be one of those people that's like, okay, I like, see the problem, like, what are my solutions for it? And if you're someone that like, likes being like, given a list of things to do or like, likes having a lot of direction from someone above you, like, you just get none of that. And so I actually, like, don't recommend it for everybody because I think people can feel really lonely or feel like they're not doing a good job. And it's just that, like, some people have the right skillset and some people don't. But yeah, I think, like, pros wise, it's like, I'm a really independent worker. I love working by myself. I don't have that, like, I wish I had co workers feeling that some people have. I like, go to lunch in the middle of the day with some of my friends. Sometimes I feel like working for yourself? For me, it's been really valuable to feel like all the work I put into what I'm doing is directly benefiting me versus, like, paying the salaries of my bosses. I think, like, people feel really resentful on teams a lot of times because they work really, really hard and care a lot about what they're doing. And then they're like, okay, like, thank you for my measly salary. I hope you enjoy your giant home. Like, it's just really frustrating, I think, you know, to know that, like, okay, I'm working on a project that's, like, kicking my ass right now, but, like, at the end of it, I'm going to get a paycheck, and that paycheck goes in my bank account, and that is my bank account feels, like, so empowering. It feels like motivating and like, I want to put more work in. And so that feeling is a huge positive. The negatives are all obvious. It's like health insurance, like. Like some months having $0 coming in, some months not having $0 coming in. It just like, it's. All the things that you know about working for yourself, they're all true. But for me, that satisfaction of building something on my own and feeling like I'm in control of my time and everything else, like, way outweighs all of those insecurities. So, yeah, that was a really long winded answer. So I hope I got everything.

[A]

You covered it all. I think you're totally right, though. When I was doing freelance writing, it was so much less stable than I even predicted it would be. Like you were saying, some months, there's nothing coming in. Some months are huge. You just kind of have to trust that the big month is coming. And sometimes it's more of a medium month, and you have to make that work, too. But it is so much more rewarding than, as you said, just working for a giant machine and being a small part of it. And I think for some people, that in itself, like, working in this bigger thing can be rewarding too. But for me, I'm totally with you.

[C]

Yeah, absolutely. I think 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. Like, you just have to hold on and wait and see. And there are so many times along the way and those, like, the first two years of me working for myself where I was like, I need to go get a job. Like, what am I doing? I'm making. No, this is the third month I've made under a thousand dollars. Like, it's not good and it's scary. And then, like, the next month I'll, like, book a big job and I'll get a. You know, I'll get to invoice for a deposit, and that will take me for through two months of rent. You know, it just. It just is being patient and Trusting that, like if you keep going and you keep putting into your work, into it, it eventually will come back. And then, you know, as you grow, those ebbs and flows don't feel like such life altering ebbs and flows. You start to save and figure out like what you need to do in order to anticipate what that looks like. And it becomes easier over time for sure.

[B]

I'm curious, you were talking about how much your industry changed during the pandemic and you know, how you valued having in house experience and I don't know if you're in touch with this at all, but like, you know, for younger people who are kind of just entering the workforce in your industry, like how do you think about finding an in house job versus going it alone from the beginning or like finding, I don't know, some type of apprenticeship given, just like how much the career path might have changed because of COVID because of the economy, etc. Because I feel like a lot of younger people like Gen Z is being forced into having like a portfolio career type situation as opposed to necessarily having the stability and being like, I have my resume, I'm choosing this.

[C]

Yeah, absolutely. It looks totally different today than it did when I was 22 and applying for jobs. Like it used to be that a brand would have like six graphic designers on their team busting out emails and now it's like they maybe have someone freelance like cranking out everything for the brand. And so it's a totally different landscape. I think that mentorship is really important and I think maybe that's like where if you're not getting kind of inside out experience on the brand side, you can still learn a lot from someone that's done it before you or someone that can kind of like push you towards learning more. You know, I didn't really have a mentor, I would say in like specifically in design, I was, there was a lot of learning as I went and I think looking back, I really would have benefited from having someone that was like 10 years ahead of me, that had done my job before me, that could say here's how I grew in this direction or here's where I invested time in developing this skill set. I was kind of just figuring it out as I went and now I try to do that for some of the younger people that I work with. I feel like some of them are 24 and have not worked in house or had an internship and that's it. And they're freelancing and that's the reality. And the more you can just learn from the people that have done it before you and be open to the fact that, like, there's a lot to learn with experience, and it just takes time. I think that's the best you can do. And I think there's. I know plenty of creatives that have been for their whole adult lives, they've been freelancers, and they're, like, so talented and successful and have built names for themselves. And I look up to them so much, too, but those people had mentors too, you know, so it's just really figuring out how to push yourself and, like, have humility. And remember that, like, at every level, there's still so much to learn and no one knows everything, so we're all just figuring it out as we go.

[B]

Isn't that the truth? I feel like I remember being at my first job and thinking that everyone older knew everything, everyone who was more senior. And the older I get, the more I realized I was like, no, they didn't.

[A]

Yeah, that's how life feels.

[B]

I feel like I know it's how life feels too.

[A]

It is, but it's a really good example of it.

[C]

Totally. I think it's, like, important to remember that, like, everyone started from zero. And some people are better at absorbing things and pursuing knowledge and pursuing, you know, gaining new skill sets than others. But, like, we're all, like, googling how to do stuff sometimes. And I'm expecting it'll be that way, like, for the rest of my career.

[B]

Well, also, the pace of innovation and change has accelerated to a point where I'm just thinking about marketing, where, you know, like, the things that were valid at the beginning when I had my first marketing job, are so different than they would be today. And even since having left doing freelance work in 2022, like, I honestly, if I had to go back to it, you know, I think that I. I do have soft skills that are still relevant, but I, earlier this year was thinking about if I was going to start picking up freelance clients again, and I was like, so much has changed in the two and a half years that I was out of that workforce that, you know, like, a lot of my experience is in some way invalidated.

[C]

Totally. Yeah, I think about that a lot, too. And it's a good case for adding more lines to your. To your portfolio career, because it's like, you know, in that time you've written a book, you're writing another book, you're working on other things, and I think that that's what's going to grow with you for Forever, right? Like, the projects that you do not for clients, but the projects you do for yourself are the things that, like, you'll build on and you'll evolve as you get older. And like, as a creative director, I often worry about, like, what age and relevance does to job opportunities for me if I ever decided to go back in house. Like, there's so many talented young people that have so many more resources than just for learning than I did. I couldn't. Like, I had no access to creative directors when I was in college. Like, I didn't have tick tock telling me what the difference between art director and a creative director was. Like, I just was, you know, doing whatever I was doing. And I think I worry a lot about, like, creative irrelevance. And I think the best way to fight those insecurities that come up every once in a while for me 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. And the more money and success and fulfillment you have in those different areas, the less you have to depend on the things where like, yeah, it's unstable. It's always going to evolve. Everyone uses Figma now. I didn't learn it. You know, it's just a different. It's a whole different thing. And so. But I'll always be me and I'll always have like, my point of view. And so that's where I'm trying to invest in for my future, just like you guys are.

[B]

That's such an inspiring place for us to end it. But I feel like we've heard about so many of your businesses, but for people who are looking for you on the Internet, where can they find more about you? Where can they find more about your design studio? Where can they find everything you're doing to check out?

[C]

A la carte on Substack is really where I put the most of myself into. It's just alilabelle.substack.com and then I'm Ali LaBelle on Instagram and Alilabelle Co is the design studio. And that's it. Don't follow me on TikTok. It's nothing. I hope to see some of you guys around. It would be fun.

[A]

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[B]

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[A]

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[B]

All right, Olivia, let's get into some n matter. What are you obsessed with?

[A]

I'm obsessed with a true crime ish podcast called Beth's Dead. Have you heard of this?

[B]

Okay, I feel like this is a sensation because I was at dinner last night and somebody else was talking about this, and I think you're probably like the third or fourth person who I've heard bring this up this week.

[A]

Okay, so this is a true crime story hosted by Monica Padman, who you might know from Armchair Expert with Dax Shepard. And it is about a parasocial relationship to these podcasters that she knows. A different podcast, Not Armchair Expert, not her podcast. A parasocial relationship that kind of goes awry. The first, I think three or four episodes are on Spotify, and I thought they were all on Spotify, but then I got to the next one and it was like to listen to the whole series join our Patreon. And I was like, God damn it.

[B]

Oh, smart, though. Smart.

[A]

I was. I am this close. I am this close to joining because it is just so unsettling. But also, as someone who podcasts, it's. It's just wild. It's so interesting. Jake and I were listening to it on the drive from the concert last night, and we were both just locked in. I think they're doing new episode drops every week or you can binge the whole series on Patreon. So I'm listening. I'm kind of tempted to go on a very long walk tomorrow and just join the Patreon, download the whole thing because it is so good. Even if you don't like true crime, I think you would be fascinated by this.

[B]

Interesting.

[A]

I don't know what turn it's going to take. Like, I think I know, but I'm on the edge of my seat. What's your obsession?

[B]

Okay, my obsession is the Lily Allen album, West End Girl, informally known mostly just on this podcast as the Ballad of Doug Cheese. I had previously, like, sampled this album. Like, I listened to A few of the songs I skipped around and I liked it. I. I don't remember what happened, but I ended up not listening to the whole thing. And then a bunch of my friends are so obsessed with it, and they were like, no, you have to listen to it front to back. No skips. It's like a story. You have to listen to the whole thing. Earlier this week, I was on a walk and I listened to the entire album. Olivia. It is incredible. It is incredible. I mean, it's incredible on multiple levels. Like, I think the album itself is just such a cool and interesting storytelling exercise where it operates as an album, not as individual songs. Like, the story unfolds from song to song, but also the female rage of releasing an album, blowing up your cheating husband the week or a few weeks before his very popular show comes back from hiatus. Like Chef's Kiss. Masterful. Incredible.

[A]

I also heard that she recorded this in something like. I want to say weeks or something, like just a couple weeks or in the span of a week or something. Something totally crazy.

[B]

I. I could be wrong. I'm obsessed with this. I'm obsessed with. I need to dig into the lore behind this now. Like, I am so obsessed. I keep listening to the album. It makes me feel good that I. I hope she has a good record contract, but, like, theoretically, me streaming this puts money in her pocket, where I'm like, yeah, let's go get a brownstone of your own.

[A]

Lily, she just announced a tour.

[B]

Oh, I would. I am going to go to that.

[A]

Get. Get those tickets. Oh, that would be. That would be the most fun London trip.

[C]

Oh, my God.

[B]

That would be so fun if you.

[A]

Like, planned a trip around that concert.

[C]

Wow. Sorry.

[B]

I've stopped paying attention. I'm now just Googling tour dates.

[A]

I fully support you.

[B]

Wow. Yeah. Obsessed. Highly recommend. Although it does sometimes bleed over. Oh, it's only in the uk. There's not any shows. Okay. We'll figure it out.

[A]

Even more reason, I do feel like, though, it.

[B]

It is making me secondhand angry in a way that I, like, listen to it. And I'm so fired up. And I'm like, oh, this is, like, emotionally, like, I'm getting very hyped up over this thing that is not real to me. To me, like, it's not.

[A]

Yeah.

[B]

I'm so angry at this man. I don't know.

[A]

I was watching a clip from the red carpet premiere of Stranger Things, and I was like, wow, he's just out here with his gigantic mustache just pretending like the whole world isn't shaking their heads.

[C]

Yeah.

[A]

Well, what about reading?

[B]

Okay, so let me tell you about the book that I read that was not yours first. So I read the book Witch by Meg Shafer, which comes out in April, and I read it on Halloween weekend, and this was just the coziest speculative novel. Oh, my gosh. It is such a love letter to readers into books. It is about a book witch who basically has these powers to jump into any book, and she does it to help if there are wayward characters who have strayed from the book to bring them back into the book. But she's also fighting against these mysterious burners who are going into stories and burning books and trying to, like, destroy books whose content they do not find suitable. Which you may feel some parallels with the real world. Oh my gosh, it was so fun and lovely and sweet. It was so cozy. It was fantastic. And then not cozy. I'm sorry to say I don't think that was an adjective you were expecting, but I fucking devoured Little One by our very own Olivia mentor. I feel like it would be uncomfortable for me to pitch your book to you, so can you give us. Have you mastered your, like, two sentence pitch for it yet?

[A]

I think. I don't think it's two sentences. Yes, I will do it. So Little One is a dual timeline story about Catherine. And in the past timeline we see her in the community where she grew up, which is a cult kind of a spoiler, but not really run by her father. And in the present timeline we see her in her really independent adult life in the city. And the story is about what happens when a journalist starts to uncover how she grew up and her past and all her secrets. Did I hit all the high points?

[B]

I think so. I think so. This was so good. I found it compulsively paced, like whenever I reached, because it alternates between the two timelines. Whenever I reached the end of one, I was like, well, I can't stop now because I need to know what's going to happen. Oh my gosh. It was so masterful. It felt so you. And I will also say for any listeners who are concerned, I felt like it was fully Scaredy cat approved. Nothing was too scary for me. Even though it is very suspenseful and thrilling at times, it was not scary in any way. So. Oh my gosh. I enjoyed this so, so much. If you hadn't already guessed, it's definitely going to be our February book club pick next year. And I cannot wait for the spoiler episode because I have so many Questions that I want you to answer.

[A]

Oh, thank you. Thank you. I'm glad to know about the scaredy cat stuff because I don't. To me, it's not that scary, but that's good to know. It's just dark.

[B]

I didn't think so. Yeah, it's dark, but it's not scary.

[A]

Well, thank you very much for reading and for that lovely review.

[B]

Everyone. Make sure to get your pre order in. You want this on launch day. Thank you. Well, what about you? What did you read this week?

[A]

I read the Good Daughters by Bridget Dale, and I read this. Bridget asked me to be in conversation with her for one of her launch events in the city, which was so nice of her. And so I read this book for that. It's historical fiction, which is not my usual genre. It follows three different suffragettes in early 1900s London and their fight for the right to vote. Bridget has her master's in women's history from Yale, and so this was like, all from the research that she did for her master's. And I read this in one day, like one morning. That's how fast I flew through it. It is very much like feminist Downton Abbey.

[B]

Oh.

[A]

And yeah, it's really fun. Is not the right word, but it just flies. I don't know if it's the short chapters, the different points of view. There's a lot of dialogue. But I really, really enjoyed this, especially because I read it very soon after election day. And so it was just a nice reminder of, like, we have to keep fighting these battles, you know, these women who fought so hard for years and years and years, the right to vote. And now, of course, we get to benefit from that. Like, there are so many other fights that we have to just keep on keeping on with. So it's a great reminder. And if you like Histor, you will devour this, I am certain.

[B]

Okay. Do you want to give us the pitch for our November book club pick? Our final book club of the year? Because we don't do a December book club.

[A]

Yes, this is the Correspondent by Virginia Evans. And this is the perfect cozy November holiday read. I think it is entirely in letters and emails and other notes. It's about this woman who has spent her whole life in deep correspondence with so many different people. Famous authors, family members, and. And it's a lot about family, really, and complicated relationships and trauma. But weirdly, it's cozy.

[B]

So, yeah, it is one of the most unique books, structurally, that I've read recently. I really enjoyed it and I thought that it sounded a little bit too slow for me from the pitch, so if you're feeling the same way, I would tell you to give it a shot. This is also it's such a cool word of mouth marketing story, kind of just the word spreading slowly. So I'm excited to talk about that too. If you would like to tell us about your career portfolio or otherwise, please join us in the Facebook group. Under Bad On Paper Podcast you can join the BFF Group, formerly known as the Geneva Group, which is basically like a chat room app. You can search under Badon Paper podcast. We are on Instagram atonpaper podcast. I'm on Instagram ecamfreeman and my newsletter is eccafreeman.substack.com I'm on Instagram and substack.

[A]

Liviamentor and if you would like to pre order little one signed copy regular copy, you can find all those links on my website or in the show notes.

[B]

See you next week. Bye.