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EP10: How Do You Run 3 Newsletters at Once? | Jessica
22nd September 2026 • Sustainable Side Hustle • Vinayak Ramesh
00:00:00 00:17:12

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Connect with Jessica: https://substack.com/@jessthecreator

Welcome to the Sustainable Side Hustle Podcast with Vinayak Ramesh.

Most people struggle to stay consistent with one newsletter. Jessica runs three, across completely different topics.

In this episode, we talk about how she went from nursing to writing online, why she pushes through perfectionism instead of waiting until everything feels ready, and what it actually takes to manage multiple newsletters at the same time without pretending it’s easy. We also get into the trade-offs of splitting your attention across different projects and what happens when one idea unexpectedly starts getting more traction than the others.

>>> Enjoyed the episode? Follow the Sustainable Side Hustle Podcast on Apple Podcasts or Spotify so you don’t miss Part 2, and leave a rating and review if you’d like to support the show.

>>> I also write every week about building income online without letting your side hustle take over your life. Subscribe to The Sustainable Solopreneur on Substack:

https://substack.com/@vinayakramesh1

Transcripts

Speaker A:

Most people struggle to stay consistent with one newsletter.

Speaker A:

Jessica runs three of them.

Speaker A:

And the funny part is, the one she never even planned to start is now the one making her the most money.

Speaker A:

Jessica started writing online while working as a nurse.

Speaker A:

Since then, she has helped build multiple best selling substack publications and now runs three of her own across health, investing and helping other creators build on substack.

Speaker A:

In part one of this conversation, we get into how she went from nursing to writing online, why she believes overthinking and perfectionism stop more people than lack of skill, what it actually takes to manage three completely different publications, and the very real burnout that comes with trying to do too much at once.

Speaker A:

I'm your host, Vinayak Ramesh, and this is the Sustainable side Hustle podcast.

Speaker A:

Let's get right into it.

Speaker B:

Hey.

Speaker B:

Hello, Jessica.

Speaker B:

Welcome to the Sustainable side Hustle Podcast and it's a real pleasure to have you here.

Speaker B:

How are you doing today?

Speaker C:

Hey Maniac, how's it going today?

Speaker C:

Thank you so much for having me here.

Speaker B:

Yeah, I mean, your experience will be very useful for our audience.

Speaker B:

So why don't you introduce yourself and talk about your journey so far.

Speaker C:

I'm Jessica on Substack.

Speaker C:

I'm Jess, the creator.

Speaker C:

My trade is, my background is in nursing.

Speaker C:

I have my master's in nursing.

Speaker C:

So I'm a registered nurse and also a nurse practitioner.

Speaker C:

I work a bit in pediatric oncology.

Speaker C:

Then I moved to flight nursing.

Speaker C:

And while I was in flight nursing, I started writing online.

Speaker C:

The site I use was called Ghost blog site and you have to promote it and everything.

Speaker C:

saw a substack at the end of:

Speaker C:

So then in:

Speaker C:

And I started writing online once a week, every Sunday.

Speaker C:

And then I, because I had saw this video about writing online from Nicholas Cole, you have to publish online for two years straight.

Speaker C:

One week, once a week for two years, so that you can prove to yourself that you're actually gonna do that.

Speaker C:

You actually can be a consistent writer.

Speaker C:

After four years of that, they ended up basically getting rid of the flight site.

Speaker C:

So they let us all go.

Speaker C:

And I started getting into trading and I was already studying trading.

Speaker C:

And then I ended up doing ghost writing for the stock.

Speaker C:

A stock market investor, trader and investor.

Speaker C:

And so I had mentioned him to make some Substacks.

Speaker C:

So we created one substack and became a bestseller.

Speaker C:

Then we about swing trading and investing.

Speaker C:

And we started another newsletter about creating income stream in the stock market with margin investing, margin trading.

Speaker C:

So that one became a bestseller.

Speaker C:

And then I had my own MP fellow become the CEO of your Health, which is my first newsletter about health and wellness, functional medicine, mental health, and then all three of them became bestsellers.

Speaker C:

I wanted to launch my second publication called Nurse in the Market, which was about navigating the stock market without fear and knowing what's going on without it sounding like you need a translator.

Speaker C:

But then I had a meeting with my mentor, Anna Cowan, you probably know who she is on Substack.

Speaker C:

She mentioned to me, why don't you run a workshop about how to create a subset from scratch in 60 minutes?

Speaker C:

And it just sounded really obvious at the time.

Speaker C:

So I did that.

Speaker C:

People signed up.

Speaker C:

And then I.

Speaker C:

When I made the workshop, I had launched that substack and didn't do Nurse in the market yet.

Speaker C:

And then I still had Nurse in the market ready to go.

Speaker C:

So then about two or three weeks later, I launched that.

Speaker C:

So that's why I have three publications now.

Speaker B:

Wow.

Speaker B:

I think you talk a lot about the overthinking trap and perfectionism as, I mean, they are the things that hold people back, right?

Speaker B:

So I mean, what is the story behind all of that?

Speaker B:

Is it something that you have experienced it yourself?

Speaker C:

I get like a lot of anxiety and overthinking as well.

Speaker C:

A lot of times when I do new things or like there's change, evolved or trying something new, I get like a lot of anxiety before.

Speaker C:

So I don't want to psych myself out, try to push through the overthinking.

Speaker C:

Right.

Speaker C:

Like the perfectionism.

Speaker C:

If I just avoided everything I didn't want to do, I pretty much not wouldn't do anything.

Speaker C:

So it's like kind of more just pushing, getting started to build the momentum to be able to push through and not actually let your anxiety or whatever friction there is get the best of you.

Speaker B:

Yeah, makes sense.

Speaker B:

And so like there is a line between moving fast as well as moving recklessly.

Speaker B:

So how do you know which one you are doing?

Speaker C:

Just feels different.

Speaker C:

You feel like you're in a more alignment, I guess, and you're actually like enjoying what you're doing and making a difference.

Speaker C:

You feel good about what you're doing things, you just go all in.

Speaker B:

You are building and figuring it out in public.

Speaker B:

Right.

Speaker B:

So you are writing and ghostwriting.

Speaker B:

You are handling your own publication.

Speaker B:

So how is it going?

Speaker C:

Like, it's been an experience.

Speaker C:

It's going well.

Speaker C:

I never really thought that I would have a publication about teaching substack stuff again.

Speaker C:

I always try to have two publications, not three.

Speaker C:

But it's been like a cool experience, like helping people with substack because I met a lot of cool people along the way and helped a lot of cool people and met people that I wouldn't have met if I wasn't.

Speaker C:

If I didn't have that substack publication.

Speaker C:

It's been growing pretty steadily.

Speaker C:

I have almost 400 subscribers and I started it six months ago.

Speaker C:

The purpose of the publication obviously is to help people.

Speaker C:

So help people with substack and make it as practical as possible.

Speaker C:

And then also it's just like a lot of people are teaching substack stuff.

Speaker C:

So you have to get creative in your own way of how you're going to teach it or where you're going to present this information.

Speaker C:

So I would say it's been like a rewarding experience so far.

Speaker B:

Oh, that's nice.

Speaker B:

That's nice.

Speaker C:

It's stressful for sure though for our university publications.

Speaker C:

Like, yeah, it's crazy.

Speaker B:

Yeah, that's true.

Speaker B:

But I would like to come back to your trading publication.

Speaker B:

So how did you get into trading and was it something you were interested in before?

Speaker C:

I was interested in it, I just knew that like a certain way to build wealth.

Speaker C:

So I started reading about the stock market and stocks and then I came across that investors like trading strategy and stuff and I started reading trading books and I basically just.

Speaker C:

I just wanted to know how to be more prosperous or how to build wealth.

Speaker C:

For my family not being in like the rat race.

Speaker C:

Another thing was just to learn actual skill.

Speaker C:

Like investing and trading are two different skills.

Speaker C:

So I mean, investing is like a great skill to know, but trading as well.

Speaker C:

Like how can we make money from anywhere with a phone?

Speaker C:

Basically, like once you learn high income skills, you can make more money and save more money and build more wealth.

Speaker C:

So I just got into trading in the stock market just because I wanted to start investing and building wealth.

Speaker B:

That's great.

Speaker B:

I mean, it's a good idea to stack up multiple sources of income, right?

Speaker C:

In America, you can really only get rich like three ways.

Speaker C:

Starting your own business that's really profitable or real estate or stocks.

Speaker C:

So there's really only three ways you can.

Speaker C:

So the stock market was faster than getting into real estate for me at least.

Speaker B:

I see.

Speaker B:

So your publication Unstuck to published is for substack for People who want to grow on Substack and the nurse in the market is for people interested in trading.

Speaker B:

And what is NP Fellow about?

Speaker C:

So unstuck to publish is for like people on substack writers and creators on substack who are surgically new or stuck with their publication.

Speaker C:

Like they need help building their publication from scratch.

Speaker C:

Like the about page and the welcome page and stuff like that.

Speaker C:

Like getting the foundations of the publication, making sure the name's correct versus a profile name.

Speaker C:

Just important things that if the person's serious about growing on substack or making money off substack, need to be in place.

Speaker C:

And then MP Fellow, become the CEO of your health.

Speaker C:

Well, MP Fellow stands for Nurse Practitioner Fellow.

Speaker C:

It's like a doctor how a new resident doctor that just graduated, they can be a fellow.

Speaker C:

This is a nurse practitioner Fellow.

Speaker C:

So it's like a nurse practitioner that's like in the first year working.

Speaker C:

So I had applied to a nurse practitioner fellowship program thinking I was going to get it.

Speaker C:

They only pick one person, but I was thinking I was going to get it or trying to manifest me getting it.

Speaker C:

And I called an MP Fellow and then I didn't end up getting the position.

Speaker C:

So then I just switched the whole topic.

Speaker C:

So the MP Fellow was going to be for like, like a hematology oncology nurse practitioner fellowship.

Speaker C:

So like a blood disorder and cancer fellowship.

Speaker C:

But I didn't end up getting it.

Speaker C:

e because this was in back in:

Speaker C:

So like back then it still is.

Speaker C:

So I just switched topics because I. I like the functional medicine approach, which is like treating the individual and getting to the root cause, which is not the conventional way, which is treating the symptoms of disease.

Speaker C:

Instead, you get to the root cause and you take an individualized approach.

Speaker C:

And then I was like making infographics and reels on Instagram and it was taking me hours to do all this stuff that was like getting no engagement.

Speaker C:

So I kind of gave up.

Speaker C:

And then that's when I started my blog on Ghost and then eventually moved it to subsect.

Speaker C:

So MP Fellow, I realized no one knows what that is except me, really.

Speaker C:

So that's why I turned it in, changed it to become the CEO of your own health, because it is about teaching or helping other people become the CEO of their health, inspire them, their individuality, promote health and prevent disease, prevent chronic disease and like inflammation and stuff.

Speaker B:

I see.

Speaker B:

So are you not pursuing that fellowship again?

Speaker B:

Or is it something you look forward to doing?

Speaker C:

Yeah, it was going to be with adult oncology patients, like adult cancer patients.

Speaker C:

I didn't really want to do anyways.

Speaker C:

I had worked with children, so it was like slightly different.

Speaker C:

I didn't want to do adults, but I was open to it if they picked me to get my foot in the door all the time.

Speaker B:

And so one thing that I want to ask is what is the trade off in running these three publications instead of just picking one and going deeper into it?

Speaker B:

How has your experience been in managing three and like what's the trade off and all in terms of time, energy?

Speaker C:

I mean, I don't see any problem with just having one publication, especially if you know what you're doing and like you're good at it and you're having success with it, like that's great.

Speaker C:

I don't know.

Speaker C:

I think it just depends on the person.

Speaker C:

It could maybe be better like to just have one and go all in, but then at the same time they're on different topics, like completely different topics.

Speaker C:

And I know if you do have one successful newsletter, you could easily have another one.

Speaker C:

Granted the audience likes the topic and all that.

Speaker C:

But I think like Nicholas Cole from Write with AI and he is in the art and business of writing and he has a fiction newsletter.

Speaker C:

I think he has three or four best selling newsletters.

Speaker C:

So.

Speaker C:

And I bring him Nicholas Cole up a lot because I read a lot of his books about writing online before starting writing online.

Speaker C:

So when I see other people doing it and being successful with it, it's like it's totally possible, undoable.

Speaker C:

But I'm not against like going all in on one publication either because I know most people aren't going to be able to handle two, let alone three inch publications.

Speaker C:

It just depends like also if one of the, if your one publication is doing so well, like I don't know, maybe just invest more into that.

Speaker C:

If I had to pick like just one of my publications, I don't know which one I'd probably pick like the health one, my ampi fellow one.

Speaker C:

But I don't know for sure, honestly.

Speaker B:

So how do you manage the time?

Speaker B:

So my attention is getting divided between these three different things.

Speaker B:

So how do you save yourself from draining yourself out and giving the time each publication needs?

Speaker C:

It's really hard.

Speaker C:

If I give each publication like the time it needs out pretty.

Speaker C:

I'm pretty much like on the verge of burnout, honestly.

Speaker C:

And when I'm not, it's probably it's because I neglected one of the publications for the week or two, the one right now that I've been most consistent with is MP Fellow or I post on that every Sunday and every Wednesday.

Speaker C:

And I think nurse in the market gets neglected the most.

Speaker C:

It's just hard to do three publications and not get burnout.

Speaker C:

If I do two articles per week for each publication, plus, let's say I do a live, which I do a weekly live, that's seven articles in one week.

Speaker C:

And it's just brutal.

Speaker C:

Like it's crazy.

Speaker C:

Let's say, like my article that came out today, I posted it last Tuesday.

Speaker C:

So like some of them I try to get ahead.

Speaker C:

But the stock market is hard because you're, you're following the market in the moment or that day to day.

Speaker C:

But I can't like really etch content like that.

Speaker C:

I don't really do that.

Speaker C:

Like I'm not gonna go sit somewhere and do just web out three articles.

Speaker C:

Like just doing one is enough.

Speaker C:

Just doing one a day is a lot.

Speaker C:

Like sometimes I'll do two.

Speaker C:

There are days when I do mine.

Speaker C:

But that's crazy if I do.

Speaker C:

Like yesterday I did two.

Speaker C:

I posted one and scheduled one in the morning I was like, I don't want to write any articles, but I'm already like, already thinking.

Speaker C:

But if I kind of stay ahead of it a little bit, it's not so bad.

Speaker C:

But like even staying ahead of it, the workload's still the same.

Speaker B:

Yeah, yeah.

Speaker C:

It takes me like two to four hours minimum an article.

Speaker B:

So yeah, I mean, it's a real effort.

Speaker B:

I think so.

Speaker B:

And you are doing this full time.

Speaker B:

It will get hectic even if you're doing it full time.

Speaker B:

So I think hats off to you for maintaining so many publications on a consistent basis.

Speaker B:

Doing it consistently for months and years right now.

Speaker B:

So it's a big thing.

Speaker B:

So I would like to ask, are all of these making you money or is it one publication that's bringing in the most of the revenue?

Speaker C:

I would say the one that makes the most money on start to publish the one about substack.

Speaker B:

Okay.

Speaker C:

That's why in the beginning when I started the substack stuff, I'd never stopped because the demand for it was ridiculous compared to the other two publications.

Speaker C:

Publications, I think like nursing the market has a potential to make the most money though, obviously, since it's about investing in trading, which is like a high income skill.

Speaker B:

Yeah, yeah.

Speaker B:

I mean, I was expecting that your nurse in the market publication would be making most money, but it's surprising that you never know until you test it out.

Speaker C:

Right?

Speaker C:

That's what I'm saying.

Speaker C:

Like, I thought the stock market would.

Speaker C:

Now it's like I'm helping people with Substack.

Speaker C:

Maybe it seems obvious, but I never had this intention to start a substack about writing on Substack.

Speaker C:

And then when I started, I realized there was a whole niche about, like, writing on Substack that was already there.

Speaker C:

I knew it existed.

Speaker C:

Like, I knew some creators, but I didn't know.

Speaker C:

Like, there was a, like a whole niche already going of people teaching sub sec.

Speaker C:

I probably just live in a hole, but, like, I started seeing where I'm like, oh, wow, there's a lot of people doing this.

Speaker C:

Not that I just didn't really pay attention before.

Speaker C:

I followed, like maybe three creators that I liked and trusted or whatever.

Speaker C:

So, like, that was a cool part too.

Speaker C:

Like meeting other people, like, involved in the niche and then just seeing how they approach substack and teach it as well.

Speaker A:

And that's where we will leave part one with Jessica.

Speaker A:

I really like this conversation because there's something refreshing about hearing the messy side of building online, too.

Speaker A:

Three publications sound impressive on paper, but as Jessica said herself, trying to keep all three moving can also put riot on the edge of burnout.

Speaker A:

And we are not done yet.

Speaker A:

In part two, we will go deeper into what she has learned from building these publications, growing on substack, monetizing them, and what she would actually do if she had to start again from scratch.

Speaker A:

If you enjoyed this episode, please follow the show and I will see you in the next episode.

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