Should I Choose Passion or a Stable Job?

Summary

Podcast Summary: "Should I Choose Passion or a Stable Job?"

Podcast: How To! with Mike Pesca
Host: Peach Fish Projects
Episode Date: June 23, 2026
Guests: India Witkin (Content Creator); Simone Stolzoff (Author, "The Good Enough Job" and "How To Not Know")

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Episode Overview

This episode tackles one of the classic questions facing many creatives and entrepreneurs: Should you follow your passion or choose financial stability? Host Mike Pesca is joined by India Witkin, a Brooklyn-based content creator and agency founder who is at a career crossroads, and expert guest Simone Stolzoff, who offers research-backed, empathetic advice on navigating uncertainty, setting boundaries, and defining personal success.

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Key Discussion Points & Insights

Introducing the Dilemma: Passion vs. Stability

• India's Background (02:00–04:30): India Witkin describes her multifaceted career as a content creator—working behind the camera, producing for big brands, and building her own agency and personal brand.
• She is torn between growing her business (and creative identity) and accepting client work that pays the bills but may not align with her values or goals.

Notable Quote

“I have three strategically three buckets and I’m trying to like water each of them like they were plants and try to keep them all going.”
— India Witkin (10:46)

Defining “Enough”: Financial and Psychological Thresholds

• Financial Tension (05:13–11:09): India wonders: should she say no to business that doesn’t "feel right," knowing it could cost her financially or professionally?
• Simone’s Framework (15:21): Simone identifies India's three core questions:
  1. When do you “burn your ships” and go all-in on your personal brand?
  2. How do you evaluate which client work is worth taking?
  3. How do you negotiate around money authentically?

Notable Quote

“Some people do what they love for work, and others do what they have to so they can do what they love when they’re not working. And neither is more noble.”
— Simone Stolzoff (03:03 & 16:13)

Balancing Multiple Revenue Streams

• Both Simone and India stress the value of diversifying income—not putting "all your eggs in one basket" (10:46).
• Simone suggests, and research supports, that those who keep a stable job while building their side business are often more successful long-term. (21:53)

Notable Quote

“It’s a common fallacy when it comes to working for yourself… those who started a business on the side of a stable job were actually long-term more successful.”
— Simone Stolzoff (21:53)

Filtering Opportunities: Money, Brand, & Fulfillment

• Simone’s “Watch Outs” (25:39):
  • Don’t design another full-time job for yourself with contract work, which crowds out your creative work.
  • Every opportunity should be filtered:
    1. Does it pay well?
    2. Does it help build your brand?
       If "no" to both, it's an easy pass; if "yes" to brand, pay can be more flexible.
• Evaluating new opportunities should prioritize alignment with your personal brand and ability to support creative goals.

Notable Quote

“Are they paying me a lot of money and are they helping me build my brand? And if the answer is no to both, it’s an easy no.”
— Simone Stolzoff (25:39 & summary at 42:12)

Vocational Awe and Setting Personal Metrics

• Simone introduces “vocational awe”—the pressure in passion-driven fields to accept poor pay or conditions because the work is “noble” (28:01).
• Defining what’s “enough” is crucial and uniquely personal.
  • Run the numbers (expenses, goals, savings).
  • Set an actual monthly target, like Simone’s $10,000/month benchmark. (29:20)

Notable Quotes

“The most important thing that work gives you is enough money to pay for your material existence. It’s a transaction at the end of the day.”
— Simone Stolzoff (27:08)

“No one else is going to define [enough] for you. That is a decision that you’re going to have to make for yourself.”
— Simone Stolzoff (29:20)

Navigating the Content Creator Grind & Algorithm Risk

• India voices concern about instability in being reliant on social media algorithms and being “locked into a niche” (35:52–36:32).
• Simone’s advice:
  • Build two support communities: peers who “get it” and a group who don’t care about your job.
  • This buffers against the rollercoaster of engagement metrics.
• Emphasize skill-building as a longer-term strategy; passion often follows expertise and confidence, not the other way around (34:04).

Notable Quotes

“You have to find two communities... one community is other people who are trying to do the thing you’re doing... and a community of people who couldn’t care less about what you do.”
— Simone Stolzoff (37:19)

Experimentation and Seasonality in Careers

• Simone and Mike discuss “seasonality” in work-life: priorities and risk-tolerance shift over time (32:59–34:02).
• Simone recommends prototyping various business approaches, then auditing which are most fulfilling and lucrative. Focus energy there (38:23).
• “End of History Illusion” (39:20): We underestimate how much our desires and identities will change—remaining open and adaptable is key to a sustainable career.

Notable Quote

“Life is all about change and reinvention… your dream is to be a content creator. Keep your eyes open to changing realities and algorithms around you… your desires, your needs, in five years from now may be very different.”
— Simone Stolzoff (40:40)

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Memorable Moments and Quotes by Timestamp

• 03:03 / 16:13 – “Some people do what they love for work and others do what they have to so they can do what they love when they’re not working. And neither is more noble.” — Simone Stolzoff
• 10:46 – “I have three strategically three buckets and I’m trying to like water each of them…” — India Witkin
• 21:53 – “Those who started a business on the side of a stable job were actually long-term more successful.” — Simone Stolzoff
• 25:39 / 42:12 – “Are they paying me a lot of money and are they helping me build my brand?... If the answer is no to both, it’s an easy no.” — Simone Stolzoff
• 29:20 – “No one else is going to define [enough] for you. That is a decision that you’re going to have to make for yourself.” — Simone Stolzoff
• 34:04 – “Build skills that are valuable in the market, that are rare, and once you have those skills you’ll have many more options ahead of you.” — Simone Stolzoff
• 37:19 – “You have to find two communities… one that ‘gets it’ and a community of people who couldn’t care less about what you do.” — Simone Stolzoff
• 40:40 – “Life is all about change and reinvention… your dream is to be a content creator. Keep your eyes open to changing realities and algorithms around you.” — Simone Stolzoff

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Advice & Takeaways

For listeners facing a passion-vs-stability dilemma:

• You don’t have to make an all-or-nothing leap; building multiple revenue streams, or “keeping a boat in dry dock,” is wise.
• Define your own metrics for “enough”—financially, emotionally, and professionally.
• Say no to work that doesn’t pay well and doesn't build your brand.
• Prioritize skill development; expertise creates more long-term freedom and opportunity than simply “following your passion.”
• Seek out both career peers and non-work communities to stay balanced.
• Recognize that your goals and needs will change over time; experimentation and audit cycles help guide your path.

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Structure of India’s Approach (as advised & summarized):

1. Sustain multiple “buckets” or streams:
   • Agency work
   • Content creation for self
   • Freelance client work
2. Audit opportunities:
   • Revenue?
   • Brand-building?
   • Fulfillment?
3. Experiment, then refine:
   • Try multiple revenue models.
   • Drop what doesn’t work, amplify what does.
4. Invest in skills and relationships.
5. Prepare for change (algorithms, market, personal goals).

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Final Words (Simone Stolzoff, 40:40)

"Pursue your passion. Go for it. Keep your eyes open to changing realities and algorithms around you. And I wish you the best of luck."

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This episode is a rich, nuanced conversation for anyone on the fence between creative ambition and stable income—delivering validation, tactical approaches, and real talk about the complexity of building a professional life that fits you.

Transcript

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[India Witkin]

changed so much in the last few years. So if you ever deviate from it. Yeah, you're not being shown to anybody.

[Simone Stolzoff]

Some people do what they love for work and others do what they have to so they can do what they love when they're not working. And neither is more noble.

[Mike Pesca]

You've probably heard the advice that if you do what you love, you'll never work a day in your life. And that's why I just constantly watch old reruns of the Muppet show and hope to get paid for it. I guess there's probably more to that advice when you really think about it. If you do what you love and the market values that you'll never work a day in your life. There's a lot of advice about doing what you love and following your passion and not settling. And in fact, it's more than advice. It's the plot of every Disney movie and most of the shows that are geared at 12 year olds. Now that we're adults, though, we have to make choices and these choices are often fraught. And here at a crossroads of her life is my guest.

[India Witkin]

My name is India Witkin. I'm a Brooklyn based content creator, podcast and video producer. And I have a little marketing agency of one, hopefully growing two more.

[Mike Pesca]

All right, so Witkin core, soon to take over the world. Know when you say a content creator, that's the content, the video, the podcasts, anything else. Any puppetry that we're leaving on the table.

[India Witkin]

I haven't branched into puppetry yet, but maybe that's, that's the next one. I do a lot of things. Video, documentary, television, podcasts, short form. I write. So really I'm just missing puppetry so

[Mike Pesca]

when, if you hear the do what you love thing and maybe you haven't heard it from other people, maybe you're just feeling it for yourself. What is that thing that you love that you want to do professionally?

[India Witkin]

Yeah, I love to create videos. It's being on camera, it's the filmmaking, it's everything in between. I've produced my own work for many years. I've produced for other people for many years. And really for me it's just the way I love to express myself and I love, for me, my, my content is mainly around being multicultural. It's being about, it's about being mixed race, it's about food, it's about history.

[Mike Pesca]

And does that video content pay the bills?

[India Witkin]

I pay my bills mostly by doing behind the camera stuff, so producing for other people. But I've, I've started to get paid for my on camera stuff. I, I just got a nice brand deal last month. That was a nice couple months of rent for me. So.

[Mike Pesca]

Really, who's branding with India?

[India Witkin]

Is this, is this all going to be in the, in the video?

[Bethenny Frankel]

I don't know.

[Mike Pesca]

I'm curious.

[India Witkin]

I mean, it's not, it's not clandestine, so it's okay. It's actually a cannabis company and they wanted to collab with me and I promoted their sleep gummies.

[Mike Pesca]

Oh, that's awesome. Did you pursue them? Did you go out and seek them or did they come to you?

[India Witkin]

They came to me.

[Mike Pesca]

Where can people see most of your stuff? Or in the world of podcasting, I'm going to say hear most of your stuff. But podcasts are increasingly seen and not heard or just incidentally heard.

[India Witkin]

Yeah. So if you wanna watch my videos, I'd say Instagram is my main platform. Ndiawitkin. You can watch me be extremely weird and silly. I have a mustache for some of my videos. I am a cultural commentator and others. And for the podcast work, really it's a, it spans the gamut. I work with a lot of different companies from Time, the Atlantic, the Progressive Network, to Sony Discovery. I, you know, contract freelance in the podcast space.

[Mike Pesca]

And so far the breakdown, congratulations on the brand deal. But the breakdown of where you get your money is mostly working for other people and now you want to transition into mostly working for yourself. Is that right?

[India Witkin]

That's right. I'd say it's mostly the money that I make is mostly coming from the podcast work and then about maybe 40% of it is coming from my little agency of one. I do the content strategy, the creative direction and I produce and fully execute all the content for a couple of my clients. So that's been growing and building, so I have them on retainer.

[Mike Pesca]

So tell me, is the question, or if it is indeed a crossroads, what you're asking yourself, is it mostly a financial question? How do you know when it's time to make the leap? Or something else? A psychological question or a cultural question? I mean, cultural in terms of, you know, you defining what kind of person you are.

[India Witkin]

So my question could be from a financial and psychological perspective, as I'm beginning to grow my business, is it really smart to say no to business? Because that's what I'm. That's what I'm coming to. That's what I'm coming to terms with is, like, if I say no to these people, that's money on the line, and that's also me growing my portfolio. But I might know in my gut this might be not a good thing for me. So I'm straddle. I'm kind of grappling with that question more and more.

[Mike Pesca]

Is the main consideration in saying no, that if you do say yes, you know, obviously you won't get. You won't be getting the income if you say no. But there are opportunity costs for saying yes.

[India Witkin]

Yeah, I guess that's part of it, too. It's like I want to keep growing my own business, but also knowing when to say no to something if I don't have the bandwidth, or maybe it's not the right kind of brand I want to work with.

[Mike Pesca]

So is the consideration with say no? It would seem to me, you know, and understand your books. I'm not sensing that it's that sort of question, like, what is the right financial criteria to say no? It's something else, right?

[India Witkin]

Mm. Yeah. I had someone who came to me who was interested in working with me. It was a new business, and they were just. They had very chaotic energy. They just started their business. They clearly didn't know what they needed, what they wanted. And for me, I kind of shrivel up and get really small when it comes to talking about money. And I do think that's a little bit of a. A gendered thing that I am trying to grow out of. But, you know, I just came back to them and I gave them a number on a proposal, and they said it was too high, and, you know, that was kind of it. And I felt my soul knew this probably wasn't the right kind of business to start working with. But I also feel like in that moment, I should have taken a slightly different approach and have asked them about money from the get go.

[Mike Pesca]

So in that situation, when you talked about their chaotic energy, I'm not sure if that was maybe a post hoc justification for having not nailed down the business, you know, a little sour grapes. But there's that other question of do I even want this kind of business? So there's a little contradiction there. You're hearing it right. Like on the one hand you're like, I really, I didn't get the business and I regret that. But on the other hand, do I really want this business? And what I'm proposing is talk me through why that's not more sour grapes in that particular instance.

[India Witkin]

Yeah, no, I mean, I hear how it sounds and you're, and you're being harsh.

[Mike Pesca]

Tough love.

[India Witkin]

And that's totally fine. Yeah. I felt in my soul when I had that meeting that I didn't know if I wanted to take this job on. And a few months ago, the number that I would have given them would have been less than half of what I proposed. So that's also me leveling up because I know I'm starting to learn more about my value and my worth and the actual, you know, what this kind of work is doing for these businesses, which in a lot of cases, they don't put any marketing spend behind anything. They're just hoping that the social media is the thing that gets people to buy their product or go and walk into their restaurant, so on and so forth. I think part of the reason why I did not really want that business was because I knew it was going to take up 50 or 60% of my bandwidth and my brain space. And really as a creator and as someone who's building three businesses, one of which is as a podcast producer, as a content creator for myself, India Witkin, the brand, and then with my marketing agency, production company, that's how I see it. I see my three businesses and I need to carve space out for India Witkin, the on camera, the person you watch on Instagram and TikTok. And I knew that if I took a client like this, I would have no time for that. And so I'm also, even if I did get the business, that would be, you know, I knew I could also ask for more money because honestly, I don't need them. Right. I can pay my bills without it, so I can be more selective, but it's just kind of like, do I prioritize growing India Witkin, the marketing agency, or do I prioritize keeping my creativity and Building my India Witkin, the personal brand that I want to. You know, I have 20, almost 22,000 followers on Instagram today and I want to have 250,000 by the end of this year.

[Mike Pesca]

So that's great. I think you did put your finger on it, at least on the question that we need answered, which is what you just said. You're looking to personally grow, but there is still a necessity to take on some clients. So here's what India is really saying. She calculates that if she spends 2/3 of her time servicing paying clients and a third building her own India ink brand, that's a good ratio. But there are questions, there are pitfalls, how to maximize that 2/3 in terms of her resources and the income that the two thirds generates. And she also knows from her time in the corporate world that if she doesn't diversify, she's cooked.

[India Witkin]

I know that I can't put all my eggs in one basket. That is the worst thing that I could possibly do. So I have three strategically three buckets and I'm trying to like water each of them like they were plants and try to keep them all going so that if you know, one of them doesn't work out or I don't find work, you know, as in any of these three buckets, I'm not.

[Mike Pesca]

We wouldn't want that. Whether India has eggs in a basket, plants to water or eggplants to sweat or de gorge, that's the word for when you put the salt on the eggplants. Anyway, she does need some help and we've got that help when How TO returns in a minute.

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[Mike Pesca]

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[Simone Stolzoff]

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[Mike Pesca]

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[Simone Stolzoff]

It's the thing that you do the thing on.

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[India Witkin]

My name is India. I'm also Indian and a lot of people on the Internet are wondering why the hell my parents name me that. Well, this is why. So these are my parents, Preeti and Christian, and they could not for the life of them figure out a name for me. And a week before I was born, my Nani, my grandmother said very casually in passing, you should name her India.

[Mike Pesca]

Well, my name's Mike, so can't do much with that. Also, no one named Mike can solve a problem of an India. We need a much better person, a much more qualified individual with a much cooler name. Someone with more expertise than some Mike.

[Simone Stolzoff]

My name is Simone Stolzoff. I'm the author of the Good Enough Job and How to Not Know. And I've also been self employed for the last six years or so.

[Mike Pesca]

Oh really? So tell me a little bit about your employment history as it might pertain to what we've been talking about.

[Simone Stolzoff]

Well, I've had a sort of meandering career. I've worked in many different industries. I've worked as a journalist, but also in tech. And then most recently before I started working for myself, I worked for this creative agency called Ideo. So I'm familiar with both the agency side of the world as well as trying to make it as a solopreneur in addition to some of the research that has gone into both of my books.

[Mike Pesca]

All right, whenever you use solopreneur or they use these portman two words, I know you have expertise. If I know anything about the business community, it's that portmanteau words equal expertise. Just look at infotainment and claymation. So hearing what India has been saying, what resonated with you, Simone?

[Simone Stolzoff]

It sounds a lot like where I was when I was just starting out on my solo path. I think I heard three questions. The first is, how do you know when to burn your ships and to sort of go all in on your personal brand? The second is, how do you decide what type of work to take on, who you say yes to as you start to get more and more inbound? And the third is, how do you talk about money in a way that feels like it's aligned with your value but doesn't leave you feeling cringe at the end?

[Mike Pesca]

Yeah, I think that's right. We talked about your most recent book. It seems like maybe the last book is also very pertinent. The Good Enough Job. Tell me about how your research and how people conceive of their work life might have something to say about this conversation.

[Simone Stolzoff]

So my first book was called the Good Enough Job, and the central argument was about the value of diversifying your identity beyond what you do for work. There is sort of an anecdote at the beginning that I think sums this up well, which is, I was a poetry student in college, and I had the opportunity to interview my favorite writer in the entire world. His name is Aneese Mojgani. And I was expecting him to give me a pep talk. You know, here I was, this sort of creative. I was about to embark on this unknown future. I wanted him to say, follow your passion, kid. And so I asked him, and he said, how do you feel about the mantra, do what you love and never work a day in your life? And he said something that I'll never forget. He said, you know, Simone, I think some people do what they love for work, and others do what they have to so they can do what they love when they're not working. And neither is more noble. And I think that last part is key. You know, here is my professional idol, a professional poet, no less, telling me that it's okay to have a job that's more of a means to an end. And so that's part of the wisdom that sort of went into that first book. And the second book, how to Not Know, is About how do you get better at dealing with uncertainty, which I think is, you know, the central question of being a self employed person in today's world.

[Mike Pesca]

But when you hear India talking, do you want to give her the pep talk like that poet of so many years ago?

[Simone Stolzoff]

In some ways, yes. In some ways, no. I think that India is at a point in her life and her career where she can afford to take risks and do some experimentation. I think there's an aspect of stability, of having a few corporate clients that would allow her to be able to experiment. But I also think that she, in her heart of hearts wants to work for herself. And the more that she's sort of anchoring herself to the stability and the certainty of the corporate world, it's holding her back from maybe some of the opportunities that may come her way if she's willing to put herself out there a bit more.

[Mike Pesca]

Not to be too crass about global advice, but do you think the advice that one might give a poet 10 years ago and the one advice one might give a pretty successful content creator in 2026, those might fundamentally diverge? Like I think there are maybe three jobs that are as unremunerative as poetry and you know, one of them is buggy whip manufacturer. So what if you weren't asking the poet who you admired, but you were asking, I'm not even going to say the wizard of Wall street you would admire, but someone in a more fun, more lucrative profession, might they have said something else?

[Simone Stolzoff]

I think so. But I think one thing that I found for myself is having a little bit of stability has afforded me to be able to take more risks. So for example, the primary thing I do with my time is write books. The sort of timeline of a book is three to five years. It's not the most lucrative path. It's not the easiest way to make a buck. But even though I've written two books in the last six years or so, I've also taken on some client work as well. And that gives me some of the air cover to really feel like I can go in on my work as an author. I think often we set up these false dichotomies where it's either you're following your passion and working as a writer, or you're selling out and working for a brand. But almost every single professional writer I know has other means of making an income beyond just their creative work.

[Mike Pesca]

And I would also guess that the books are great advertisements for the other work. Your name on the book maybe inspire someone to hire you just as a compelling social media video might hire someone to hire you to do the same for them.

[Simone Stolzoff]

Yeah, that's what I heard in India's response that I would hope to bring to her, which is there's different types of client work. There's client work that will allow you to build a portfolio to show off the type of work that you want to do more of. There's client work that will help build your brand because it'll allow you to get your name out there to be sort of the face of the campaign. There's client work that's really lucrative, where the money is so good it's going to be hard to say no. And those are all things that are very different from, say, selling out to do some client work that isn't well paid, where you don't get notoriety and where you don't respect what they're trying to bring to the world.

[Mike Pesca]

Were you beset by any version of self doubt ever?

[Simone Stolzoff]

Oh, it's my constant. The cliche is that you write the books that you need to read. And part of the reason why I wrote how to Not Know is because I am a naturally self doubting person. I love to ruminate, I love to play my own devil's advocate. But I think in some ways that self doubt is the price you pay for being able to put yourself out there and have a lot of autonomy over how you're spending your time.

[Mike Pesca]

For you, was the self doubt equally spread among all the various aspects of Simone Inc. Or was it more acute in the work that you wanted to generate the books that you were writing and wanted to write?

[Simone Stolzoff]

For me, it's more self doubt about the future, particularly because I just had a kid. And so I really think about the financial piece of am I doing work that allows me to provide him with enough stability and opportunities for him to live? I don't feel as much doubt when it comes to the actual work I'm putting out into the world.

[Mike Pesca]

So the one other thing I want to ask you about is something you said, which was also implied in the mindset that India was conveying to us. Burn your ship. So this comes from the idea that Cortez has supposedly burned the ships and there was no going back and they'd have to go forge through the wilderness. I don't know how well it worked for him, but why do you have to burn your ships? It's great, right? It's. Every high school coach will tell that to his kids and maybe get, you know, an extra bit of vim on. On touchbacks or something. But why do you have to burn your boats? Shouldn't you just keep a boat or at least a dinghy or burn half the boats or, you know, just put the boats in dry dock?

[Simone Stolzoff]

Yeah, I actually don't think that you have to burn your ships. I think it's a common fallacy when it comes to working for yourself. When there's been some research on entrepreneurs that have started businesses on the side of a stable job and entrepreneurs who have just gone all in right away and they found that those who started a business on the side of a stable job were actually long term more successful. Which might feel a little counterintuitive, but it makes sense to me because when you have that stability of knowing at least some of the sources of income, it allows you not to just reach for the first idea. You have to be a little bit more deliberate and be a little bit more methodical about how you actually approach your independent work.

[Mike Pesca]

All right, so in a minute we're going to be joined not only by India, but I am going to pitch Simone my business idea, a reclamation of charred boat hulls. We'll see how that works out when hull to Sorry. How to continues Foreign.

[Progressive Insurance Announcer]

This episode is brought to you by Progressive Insurance. Do you ever find yourself playing the budgeting game? Well, with the name your price tool from Progressive you can find options that fit your budget and potentially lower your bills. Try [e-mail] Progressive Casualty Insurance Company and affiliates Price and coverage match limited by state law. Not available in all states.

[Mike Pesca]

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[Mike Pesca]

We're back with how to. And here is the pairing that I know everyone's been waiting for. Simone, listen to India's story of what she wants to do to go after to go for it on her own. India has been listening. Am I right? We'll unlock you from your secure chamber. You've heard all of this, India? I have. Okay, so what do you think?

[India Witkin]

I'm getting some good validation here from what you're saying, because I do feel like I'm taking your advice already. Not burning your ships is kind of what I have instinctively done by keeping these three lanes open, but also being strategic about it. And maybe not going 100% all in, but, you know, maybe 25%, 75%, or

[Mike Pesca]

wouldn't that be called some in or most?

[Simone Stolzoff]

I hear that.

[Mike Pesca]

That's another thing. I mean, I don't know, maybe this has no point in the conversation, but it does seem like we're drawn to bold declarations. Everything about entrepreneurialism and business. And if you went to a conference, they'd be telling you this stuff. But we say all in and burn your ships. But then when we talk about, it's like, oh, yeah, definitely don't do that.

[Simone Stolzoff]

Well, I'll give you some watch outs. I think it's smart to be able to have a diversified source of income, to be able to have multiple revenue streams, multiple ways that you're spending your time. Here are a few things I'd watch out for. One is you basically designing another job for yourself, so taking on so much contract and corporate work that you no longer have the time to commit to your creative practice. The second thing is losing sight of your North Star. I hear pretty clearly in your voice that ultimately what you want is to run India Corps. You want to be self employed and spending the majority of the pie chart of your time making videos on social, doing cultural, storytelling about food, and being able to be your own boss. So I would evaluate each new corporate opportunity that comes your way through the lens of are they paying me a lot of money and are they helping me build my brand? And if the answer is no to both of those questions, I think it's an easy no. And if the answer is yes, they're helping me build my brand, then maybe you're willing to accept a little bit less money. And if the answer is no, they're not helping me build my brand, maybe that's where you demand a higher rate.

[India Witkin]

Yeah, that's really good advice, Simone in

[Mike Pesca]

India, talk some more. And India told us she had really recently taken a meaningful sabbatical that reoriented her and gave her a new perspective. But listen to how Simone talked about India's Eat, Pray, Love excursion.

[Simone Stolzoff]

And the point that I try and hammer home is that work can be a source of meaning, of purpose, of identity, of community, all of these things. But the most important thing that work gives you is enough money to pay for your material existence. It's a transaction. At the end of the day, any job is an exchange of your time and your effort for a paycheck. It certainly can be much more than that. But thinking about work in those crass terms, especially in a world that often tells us to like, follow your passion or find your vocation, or if you haven't found a calling, keep searching. And so I think that's actually a helpful framework for how you think about this next step as a solopreneur.

[Mike Pesca]

But may I ask what happens? I mean, India's ideal job and, and a third of her job now is that self actualization expression of herself. So does the calculus change when that's in play?

[Simone Stolzoff]

There are different things to watch out for. So in the book I write about this concept called vocational awe. I love the term. It's basically in passion driven fields like journalism or storytelling or being a teacher or in healthcare. Poetry, there's often poetry. There's often a halo effect associated with the industry itself that can provide air cover for people to accept a lot less than they deserve. So one line you get in journalism, for example, all the time is there's a line of people out the door that would happily take this job. Or a line that my wife who's a teacher gets all the time, is people don't do this type of work for the money. Thank you for your service.

[Mike Pesca]

Oh my God. And a public radio journalist gets both.

[Simone Stolzoff]

But that mentality is obfuscating the actual material needs of a job which is typically pay you enough to live. And so I think that's one watch out. Especially as India pursues a more sort of creative, self actualizing path. Sure, in the short term you don't necessarily have to be raking it in. You can think about an investment of say, I Don't know, three, six months a year while you're still trying to find your sea legs. But at the end of the day, you have to think about the viability of the path as well.

[India Witkin]

You said something about having enough. How do we know when we have enough?

[Simone Stolzoff]

It's a great question because no one else is going to define it for you. That is a decision that you're going to have to make for yourself. But the first thing that I'll say is you should run the numbers. You should figure out, how much am I paying for rent, how much are my expenses when it comes to food, travel, all these other things that I want for my life. And one of the things I did early on when I started working for myself is I said $10,000. I want to make $10,000 every single month. And that will be the baseline to pay for my material existence living in an expensive city like San Francisco. And once you have a number, that can be a nice anchor so that your definition of enough isn't just sort of like more to the moon. I think people fall into this trap on social media all the time, where they're just using a vanity metric like the number of followers you have as a proxy for success. Whereas what actually determines success, in my mind is resonance with your audience and alignment between how you're spending your time and how you actually want to be spending your time. So I would advise you to do this as an exercise for yourself, both from a more empirical sense, understanding what enough is for your life right now, understanding how much money you want to save to plan for your future, and then also understanding, psychologically, what does enough mean to you? What is your definition of success, not mimicking someone else's career path, but defining for you, India, what does it mean to be a successful solopreneur or content creator?

[Mike Pesca]

I gotta say something. Sometimes I identify more from the parent angle than the practitioner angle. And if I was India's mom or dad, I'd be how old I am or older and not understanding the ways of the Internet. But I'd be specifically nervous about the whims of the algorithm, the specifics of getting into the field she wants to get into. When this algorithm has so much control over your life, I find it very scary. Am I just being generationally obtuse?

[Simone Stolzoff]

Yes. And I think there's some wisdom there. There is an actual, viable, sustainable path as a content creator, and I think one of the more durative assets you can build is a personal brand these days. It's not just something that is a game that young people want to do because they want to copy their favorite creators. It's a real industry and it's important to make sure that you also know what is your fallback plan if shit hits the fan, if you burn out, if people stop watching your videos, if you realize that Instagram is deteriorating your mental health. And so that's why I think now is a nice opportunity for you to shift the pie chart towards more of your personal brand. Because you don't have dependents, you don't have a mortgage and you've worked in the world for eight years and you have some marketable skills. But maintain those relationships, keep your network strong. Don't sort of cordon yourself off from this hand that has fed you for the last eight years. Make sure that, you know, okay, this might dry up, this might not last forever. How can I make sure that I have a fallback plan as well?

[India Witkin]

Yeah, this does feel like the time to experiment, to try. I'm very lucky that I don't have, you know, ailing parents or I don't have a lot of expenses every month. I don't have kids, I don't, I don't have a mortgage, I don't have a car. So these, these are the days I need to take these risks. And that's been a big priority the last two years. And I feel like I've learned and experimented a lot and I'm going to continue.

[Mike Pesca]

Yeah. Do you find that at different stages in people's lives, people want different things in terms of the material comfort that the job can provide versus the self expression that the job can provide? I find this to be true. I find this that in the 20s and the 30s, like you're so invested in your job, your job is you. And then maybe having moved on, I've done that. And what I really need to do is make sure, you know, my kids can go to a decent fencing camp.

[Simone Stolzoff]

Yeah. I definitely believe in both the seasonality of our own careers and our own lives and the sort of temporal nature of the needs you have when you're 25 are very different from the needs you have when you're 50. But when it comes to young people pursuing their passion or, you know, chasing their dreams, one thing that I'd say is it's also important to build skills. My favorite career book is by this guy named Cal Newport, and it's called so Good They Can't Ignore youe.

[Mike Pesca]

Yeah, he's great, by the way.

[Simone Stolzoff]

It's sort of a pushback against this idea that we should just follow our passion and the money will follow. And what he says is what you should actually do is build skills. Build skills that are valuable in the market, that are rare, and once you have those skills, you'll have many more options ahead of you. I think sometimes when I speak to young people, you know, recent college grads in particular, they want sort of what's at the end of the path without being willing to take the hike. And you have to be able to do the work to build a network, to build skills, to build a sense of how your skills can be marketed in order to be able to get paid for the things that you love doing. So I often think passion is the result of hard work, not a necessary precursor to finding it. Once you get good at something, you're gonna start feeling more passionate about it because you learn the subtleties in the art of the craft itself.

[Mike Pesca]

Yeah. This literally goes back to Adam Smith and the wealth of Nations. Here's another question specific to the field that you've chosen, India. Have you read. And maybe, Simona, you could weigh in on this, too. I've read a lot about the grind of being a content creator, especially when you're your own project, and it seems there are a lot of pitfalls there, and you have to keep putting it out and putting yourself out there, and it just seems very different from another passion project. If what you wanted to do was make beautiful canoes, that would be one thing, but what you want to do is put out content that's not only about yourself, but it is largely about yourself. Have you thought about that, India? And what do you do to guard against those pitfalls, if anything? Cause I know right now you're just trying to get there. You're just trying to climb the mountain.

[India Witkin]

Yeah. I mean, it's a lot of emotional and, like, physical mental work, just constantly putting yourself out there and reworking something that, you know is hitting. For me, I've. The algorithm has changed so much in the last few years. And what I've noticed now is that Instagram in particular, once you start posting enough and you've gotten some traction, it understands you in a very small niche. So if you ever deviate from it.

[Mike Pesca]

Yeah.

[India Witkin]

You're not being shown to anybody.

[Mike Pesca]

Yeah, that's a pitfall. So you're locking yourself into this thing that you're doing now, which is, you know, your content, about your food and your culture and your name.

[India Witkin]

Yeah, like I'm at the whims of an algorithm. The algorithm can just choose not to show me to people anymore. It feels like a lack of control. That feels scary for sure. And then also like, I don't want to only do one note. Me being, you know, Indian American, my name and you know, being mixed race. I want to do serious stuff, I want to do funny stuff, I want to do all sorts of stuff. And it feels though, as though if I stick with this path as a content creator, the only way I'm going to be able to do other things is if I keep creating new accounts, which is just extremely exhausting because then you have to, you know, you have to feed the algorithm at least three posts a week to just.

[Mike Pesca]

And then pretend your name is Belize or Honduras or Albania. It just gets grind you down, man.

[Simone Stolzoff]

I have two pieces of advice for you. I think you have to find two communities and one community is other people who are trying to do the thing that you're doing. These are your colleagues. When you're self employed, you don't have the infrastructure of having, I don't know, Slack or Microsoft Teams to shoot the shit and talk about the changes in the algorithm. You have to go out and build that community yourself. And the second thing I'd try and find if I were you is a community of people who couldn't care less about what you do for work. I think it's so easy to fall into the trap of thinking my Instagram presence is my world. And on days where my posts are going viral I feel great. And on days where my posts aren't going viral I feel like shit. And it's really important to have a community of people that can buffer you from that myopic worldview?

[India Witkin]

Yeah, absolutely. You know, you are a successful author. Was there a moment that you feel was that moment of, okay, I'm going to take a risk, take a really deliberate step forward in committing to yourself as an author.

[Simone Stolzoff]

Yeah. So the moment was about six months before my first book came out, I decided to leave my full time job. I wrote the majority of my first book on the side of a full time job where there's little irony about writing a book about work, life, balance on the side of a full time job. But in that first year, when I put out that book, writing books wasn't the only thing I did. I took a very broad approach. I was writing books, I was contributing articles as a freelance journalist, I was doing some public speaking, I was doing some editorial consulting for companies and newsrooms and I was teaching a class. And so I had this sort of multi pronged way of trying to make money. After that first year, I did an audit and I asked what is paying me the most and what is the most fulfilling? And then I did a culling. And now I basically just write books and do public speaking. And so that can be an approach. You sort of prototype different paths. You figure out what is worth it for you. And from that data, you can figure out what you want to double down on or what you might want to prune. But I think it requires you to be able to run those experiments to actually find out. It's not just a thought experiment that you'll do in your head. It's something that needs to be borne out in reality so you can get the information from the world about what you need to know. One last study that I think would be a nice thing to leave you with was this psychological study called the End of History Illusion. And it was by this Harvard professor, Daniel Gilbert, who is a famous happiness researcher. And he basically found that when we think back to our history, our lives, it's really easy to see all the ways that we've changed, all the ways where we're different from the version of who we were 10 years ago. But when we think forward, we often think that we're fixed in place. That's why it's called the End of History Illusion. We think that our needs and our tastes today will remain consistent for the rest of our lives. But the upshot for me is that life is all about change and reinvention. Right now, today, on the Precipice of turning 30, your dream is to be a content creator. And I want you to be able to pursue that dream. And I want you to keep your eyes open. That your desires, your needs, in five years from now may be very different from what they are today. Think about what you wanted five years ago and how different that is from what you want today. And so pursue your passion. Go for it. Keep your eyes open to changing realities and algorithms around you. And I wish you the best of luck.

[India Witkin]

Thank you, Simone.

[Mike Pesca]

Excellent. Simone Stolzoff is an author of the Good Enough Job and How not to Know. Thanks so much, Simone.

[Simone Stolzoff]

Thanks for having me.

[Mike Pesca]

And India Witkin is. Oh, what isn't she? She's a content creator. She has an Instagram page. As you know, she has a burgeoning worldwide corporation. India. Thanks so much.

[Bethenny Frankel]

Thank you.

[India Witkin]

Thanks, Mike.

[Mike Pesca]

If you like what you heard today, please give us a rating. Please give us a review. Apple podcast. They have a site to do it every Spotify episode. You could do that I'm not going to name all the podcast players where you could leave us a review, but it'd be great if you did. We also need your questions. Questions that start with the words how to. Email them to how [e-mail] today on my daily show, the Gist People are able to accept the complexity of other human beings and love them in their

[Simone Stolzoff]

own lives in a way that they don't seem to be able to do

[Mike Pesca]

anymore in politics and history. And that's one reason why we're at each other's throats as Americans. How to is produced by Jeff Craig and Cory Wara. Michelle Pesca puts the can do in How To. Charles Duhigg founded the show with two criteria for every segment in mind.

[Simone Stolzoff]

Are they paying me a lot of money and are they helping me build my brand?

[Mike Pesca]

No and yes, but not in the way you'd hoped. I'm Mike Pesca, back every week answering your questions of How To.

[Progressive Insurance Announcer]

This episode is brought to you by Progressive Insurance. Do you ever find yourself playing the budgeting game? Well, with the name your price tool from Progressive, you can find options that fit your budget and potentially lower your bill. Try [e-mail] Progressive Casualty Insurance Company and affiliates Price and coverage match limited by state law. Not available in all states.

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