The 7 Biggest Challenges Newsletter Creators Face

34 newsletter creators shared what they struggle with the most

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What is the most challenging part of running a newsletter and how do you handle it?

We talk about the success stories of newsletter businesses all the time.

But, we should also acknowledge that success doesn’t happen overnight, and most of these creators struggle with real challenges like yourself.

I asked the above question to 34 successful creators I’ve interviewed.

Here are some important findings based on their answers:

  • 30 out of 34 creators mentioned significant challenges they face

  • 4 creators who don’t find building a newsletter challenging leverage their prior know-how about scaling businesses and building systems.

  • Newsletters with tiny and large list sizes share similar challenges in some cases.

  • Challenges related to content quality and consistency are the biggest struggles that creators have.

  • Monetization is mentioned by only 1 creator, along with content and growth.

I grouped the answers under 7 key categories based on the most emphasized aspect:

  1. Maintaining consistency without compromising content quality

  2. Generating a continuous stream of original ideas

  3. Growth

  4. Self-doubt

  5. Business operations

  6. Absorption

  7. Copycats

    Bonus: Which challenge?

Let's dive in for more details about what successful creators struggle the most and how they handle these struggles. 

And always remember that you’re not alone in this.

P.S. What is your biggest challenge? Reply to this e-mail and share your biggest challenge so that we can chat about it!

1. Maintaining consistency without compromising content quality

  • This is by far the biggest category.

  • We previously discussed that consistency doesn’t only mean publishing regularly. It also means delivering a certain level of quality with the content of each issue continuously. Most creators highlighted this reality.

  • We also see that finding time to maintain consistency is difficult when having a full-time job.

  • It is critical for the creators with an interview format to prepare the issues beforehand since they depend on other people.

Interview Date: February 5, 2023

# of Subscribers At the Time of Interview: 28,000

The most challenging part is staying consistent.

Sometimes you’re traveling, tired, and only have half an article complete…but you need to grind it out and get something quality out the next day.

I handle it by knowing if I let one article slip, more could follow. The compound effect works in both directions.

Interview Date: February 19, 2023

# of Subscribers At the Time of Interview: 450

I think it’s consistency. It’s so easy to fall off the bandwagon. Especially when you’re running a business.

Mostly time flies so fast! It feels like you’ve just sent your newsletter and bam! Here it comes! Another Monday! Sometimes, it can get tiring, but it’s crucial to tap into our energies and find a system that works for us.

Interview Date: April 2, 2023

# of Subscribers At the Time of Interview: 800

For me, it’s the pressure I put on myself to deliver a certain quality and quantity.

What helps me is to realize that I don’t have to do it all by myself, and it doesn’t all have to happen now.

I try to focus on what I enjoy working on and how I want to add value to others and outsource some of the other tasks.

I have a full-time job, so although I have limited time, I do have a salary that I can use for this purpose.

Interview Date: April 9, 2023

# of Subscribers At the Time of Interview: 22,500

Creating something I feel good about consistently, week after week, for 150+ weeks is challenging.

This is a side project for me, so my day-to-day work is my priority — my newsletter has to fit in my evenings/weekends/early mornings/late nights and that can be challenging when I have to make trade-offs.”

Interview Date: June 25, 2023

# of Subscribers At the Time of Interview: 14,000

Quality control.

Every day has to be great. It’s a constant challenge to make sure we’re covering the most important stories, seeing the big picture, and extracting insights our readers will find valuable.”

Interview Date: May 21, 2023

# of Subscribers At the Time of Interview: 11,000

The most challenging part of writing a newsletter is… writing it.

If you have high standards, it’s a painful process to get it right.

But you have to go through it.

It’s like lifting weights.

You do that last three squat reps despite your brain shouting “STOP!” to grow muscle.

And after the training, you feel great.

I feel the same after finishing a piece.

And how do I make it easy?

I accept that it cannot be perfect. It only has to be good enough (for me). This reduces the pressure.”

Interview Date: April 16, 2023

# of Subscribers At the Time of Interview: 6,000

I get frustrated on those weeks when I’ve written a piece and think it could be better but I just don’t have the time to improve it. 

I’m committed to getting this sent every single Monday at 7:01am. This means no matter where the piece is at, I’ve gotta start posting it on Sunday.

Now, crazy as it seems, some of the articles I thought were really bad turned out to be some of my biggest crowd-pleasers. Who knew.”

Interview Date: August 27, 2023

# of Subscribers At the Time of Interview: 50,000

As a writer, the time it takes to put out a perfect product on a daily basis on a subject that has SO much information is very hard. 

Not to mention the subscribers all have different feedback on content they want to see in the newsletter. So focusing on content perfection combined with growing the audience, deliverability and monetization is a hard task.

Having a very talented writer like Ian takes away the content stress.

The back-end work of newsletters (growth, tech, monetization) will never go away. We need to continue to put in the work to grow at all costs!”

Interview Date: November 12, 2023

# of Subscribers At the Time of Interview: 60,000

“Staying consistent!

I’m reminded of this quote by James Clear:

“You do not rise to the level of your goals. You fall to the level of your systems.” 

Without a system in place for: 

1. Generating and validating ideas

2. Writing content

3. Scheduling content

4. Distributing content

It’s a very tall order!”

Interview Date: May 7, 2023

# of Subscribers At the Time of Interview: 7,800

“The most challenging part for me is pulling the story out of all of the research. Sometimes, Friday rolls around and I feel completely lost as to what the main points are.

I inevitably end up figuring it out, but that makes the process a little stressful.”

Interview Date: June 11, 2023

# of Subscribers At the Time of Interview: 12,000

My newsletters are curation based and that can be quite challenging.

I have to keep a backlog of content ready to go to ensure I have something to share on down weeks where I struggle to find anything valuable.

Interview Date: January 21, 2024

# of Subscribers At the Time of Interview: 23,000+

“Maintaining a consistent flow of content.

We understand our responsibility to provide content that dictates the lives of thousands of families and kids.

“So, we need to balance creating quality content with creating consistent content.“

We’re working on building out our content team so that Raising Empowered Kids can achieve this balance at scale.”

Interview Date: January 15, 2023

# of Subscribers At the Time of Interview: 3,100

When you are running a newsletter with interviews, you are dependent on others and need to make sure you find interesting stories, get input, send them reminders etc.

I set up an Airtable base that really helps me to keep track of everything and everyone (interviews, ads, cross promotions etc.). 

Interview Date: March 12, 2023

# of Subscribers At the Time of Interview: 1,750

Nothing is overly challenging as it’s a fun process and relevant to my interests but the one important part is to have interviews lined up in advance. Otherwise, it can cause stress if left to the last minute.

2. Generating a continuous stream of original ideas

This group of answers goes hand in hand with the struggle to stay consistent. But, there is more emphasis on the difficulty of finding new topics to write about.

Interview Date: January 22, 2023

# of Subscribers At the Time of Interview: 1,300

Originally the challenging part was making the time every day to do it, but that quickly became an advantage rather than a challenge.

Now, the biggest challenge is having something in the “From me.” section, some piece of valuable content that I created to share with my audience. 

I have a lot of different content online, but I always want to create more, but I don’t always have the time to get it all done. Keeping ideas on the shelf is probably what’s most challenging.

Interview Date: March 19, 2023

# of Subscribers At the Time of Interview: 3,000

The most challenging part is the actual writing.

As I’ve been writing about newsletters for nearly a year now, it’s becoming a little harder to come up with original content that’s still helpful to readers, informative, and interesting. I need to put more time aside to brainstorm, research, and remix article topics.

All that aside, simply finding the time to write with a full-time job, a wife and two kids, and training for a triathlon (not to mention social obligations, extracurricular, and sleeping…) is always a challenge. I’m very grateful for an understanding & supportive wife who gives me time to work on the newsletter.

I haven’t struck a perfect balance between it all, but I’m getting there.

Interview Date: April 23, 2023

# of Subscribers At the Time of Interview: 12,200

“I think the most challenging part is constantly coming up with inspiration for fresh ideas and topics to write about.

Lately, I’ve handled it by owning up to my audience when I don’t know what to write. That’s been incredibly freeing.”

Interview Date: September 17, 2023

# of Subscribers At the Time of Interview: 9,000

If it has been a particularly slow news month in the area we’re covering, there could be less to talk about, but so far I’ve always managed to find interesting items or products to include.

Some weeks, the subscriber numbers aren’t growing much and I think, “Well, have we peaked?” But then it’ll double the next week and I realize I need just to stop looking at those reports!”

3. Growth

Some key aspects of this challenge are not having a proven way of managing organic growth and the ups and downs along the way.

Interview Date: March 26, 2023

# of Subscribers At the Time of Interview: 2,200

Growth is hard.

There are so many newsletters and information sources now that it’s a streetfight for attention. It’s very hard to stand out.

I don’t have any insights on handling this other than being willing to try new things and constantly learn.

I should be doing more to promote and distribute my newsletter, but I don’t enjoy it.”

Interview Date: Jun 18, 2023

# of Subscribers At the Time of Interview: 92,000

Personally, writing the newsletter comes naturally to me.

It’s scaling it organically which is challenging. I think most people in this business would agree.

I handle it by reminding myself that nothing (literally nothing) worth doing in life is easy.

Interview Date: June 4, 2023

# of Subscribers At the Time of Interview: 2,620

Growth is most challenging, mainly when an article flops relative to my expectations. 

At some point, I'll likely solidify a sustainable approach to growing Stat Significant, but my current trajectory includes some high-highs and low-lows.

Over time I've gotten used to the ups and downs.
When a post performs well, I try not to envision myself as the world's next Freakonomics, and when a post performs poorly, I remind myself how fortunate I am to be writing for a non-trivial subscriber base.

It's not the most flashy advice, but I consistently remind myself that Stat Significant has gone further than I ever anticipated and that I should remain grateful for this success.”

4. Self-doubt

Building a newsletter requires patience and perseverance, which makes self-doubts an important companion throughout the journey.

Interview Date: January 29, 2023

# of Subscribers At the Time of Interview: 7,600

The challenging part is overcoming imposter syndrome. 

“Who am I to talk about this” is a constant companion on my journey.

But the most rewarding part is the answer to this problem: getting feedback —good or bad— from my audience. No matter if they love or hate it, at least they READ it. That’s all I need :)

Interview Date: May 14, 2023

# of Subscribers At the Time of Interview: 59,000

The hardest part for me is just the self-doubt and constantly second-guessing yourself.

I often feel like something I’m writing is terrible or is going to feel to obvious or too personal and uninteresting to my readers—but I often I find those are the issues that people connect to the most!

I think I deal with it by just “trusting the process” of writing consistently every week, even when it feels like I don’t have much to say.”

Interview Date: Dec 10, 2023

# of Subscribers At the Time of Interview: 42,000+

“I thought I’d say sticking with it and being consistent, but that is less of a challenge for me now. After almost 9 years of doing this, I’ve more or less built this habit into my life and it’s hard to imagine what it would be like to not do it. 

Honestly, the hardest part is the emotional and psychological roller-coaster you go through, especially if you want your newsletter to be a sustainable business.

There is most definitely a trough of despair you have to cross, in which you don’t know if what you’re doing is working or not; I won’t tell you to blindly persist, because if you think it isn’t working, you might be right! That’s what I struggle with the most – should I take the newsletter in this direction or that direction, would that make it more successful?

But then I have the challenge of, when I sit down to write, what comes out is what comes out – I’m not really in charge of that. There’s some other part of my brain that’s not under my conscious control that decides that.

I think that’s just the way I’m wired.”

5. Balancing business operations

Other important challenges are approaching this content channel as a business and balancing content creation and business operations.

Interview Date: August 13, 2023

# of Subscribers At the Time of Interview: 7,000

Running a business isn’t philosophically compatible with journalism since the latter is contingent upon skepticism and humility, and the former requires you to say with confidence that you’ve created the best product on the market.

Interview Date: January 29, 2024

# of Subscribers At the Time of Interview: 12,000+

“I’d actually say there are three big categories.

The first is content. Unlike finance, crypto, or marketing, there’s no news about B2B sales coming out every day. Also, there are only so many posts you can make about the best ways to cold call and cold email. Finding an interesting story is tough, but I think that’s what makes our content special. 

The second is growth. Like everyone, I want to grow bigger, faster. There’s really no silver bullet to this. Just stay the course and keep pushing. 

The third is monetizing. Sponsors are great, but you constantly have to work on getting new ones, and that’s sort of a full-time sales job itself. I’d love to find another source of revenue, I just haven’t figured out the perfect product/service yet.”

6. Absorption

Sometimes, all you can think of is your newsletter, which can be too much.

Interview Date: January 8, 2023

# of Subscribers At the Time of Interview: 14,000

The most challenging part is the newsletter is always on my mind.

I see everything I do now through the lens of “is this a newsletter topic?”.

It’s a blessing and a curse

Interview Date: February 26, 2023

# of Subscribers At the Time of Interview: 60,000

Burnout.

I take extended breaks. If I am not feeling it, I can take 1-2-3-4 weeks off until I start itching and concocting new issue ideas.“

7. Copycats

Copycats are everywhere. On the positive side, they push you to deliver the highest quality with your content.

Interview Date: September 3, 2023

# of Subscribers At the Time of Interview: 12,000

“Operating a newsletter that is mostly other people’s content while also “building in public” and sharing your wins publicly has led to multiple copycats over the years, some even directly copy/pasting from Workspaces.

This is incredibly annoying but there’s really nothing you can do about it. Just continue to be better than them.”

Bonus: Which Challenge?

Here is the good news.

Once you build your systems and accumulate enough business experience, the challenges might not be challenges anymore.

Interview Date: October 1, 2023

# of Subscribers At the Time of Interview: 9,600

“Honestly, I can’t think of any challenges.

The biggest piece of advice I have for newsletter operators is to delegate everything on the back-end of your newsletter operations to a Virtual Assistant.

I think most creators think too much of themselves as solopreneurs and do all the work themselves, which is not the smartest move, in my opinion.”

Interview Date: October 15, 2023

# of Subscribers At the Time of Interview: 80,000

“This sounds bad but, compared to my last company (a venture-backed startup), running a newsletter has been pretty easy! It's fun. I know that's not a satisfying answer.”

Interview Date: July 2, 2023

# of Subscribers At the Time of Interview: 6,280

“This might be an annoying answer and somewhat philosophical, but in my opinion, businesses should not be hard; they should be repetitive. The repetitive nature should be what’s challenging. If a business is hard, it means one of the systems isn’t working properly.

I have systems built around everything. My goal is that I need to treat myself like a computer and just put myself through the processes I've designed so that they can be highly unemotional and exclusively data-driven.

For example, with Twitter I ran tests in the beginning to gauge engagement. Here’s how it worked:

I wrote down on a piece of paper 3 hypotheses for topics people would be interested in that could be a part of my newsletter funnel. These 3 topics were exclusively what I was allowed to tweet about and if one of the 3 topics worked after 2 weeks, then I double down on the one that worked. Over time I kept doing this; pick 3 topics and select the best performing. Then scrap the 2 underperforming and add 2 new topics to pair with the top performer. Then see if any new topics perform well and replace the one underperforming until I got 3 high-performing topics. The topics I ended up with were:

1. Newsletter

2.Reddit Strategies and

3. Success Posts

Those are the only 3 topics I'm allowed to post about. That’s it. So every Sunday, I write all my tweets through Wednesday. Then Wednesday, I write them through the rest of the week. There’s some ad hoc posting but generally speaking, it can be as automated as I decide it to be.

My whole business is built and structured this way. I have a system around everything. The Reddit strategy as well.

Over time this gets repetitive, but I've built processes around things that are working currently; therefore, they’re not hard, just repetitive. Then when a process breaks in the future, I design a new system.”

Interview Date: August 20, 2023

# of Subscribers At the Time of Interview: 5,000

Writing is my best skill so I find publishing easy rather than challenging, but also I’ve been sending at least one email a week for over a decade now, from before newsletter businesses were a thing and I was sending personal updates with links to blog posts I had written.

It’s a muscle and habit I’ve built up.

ICYMI - The Latest Newsletter Circle Interviews

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    "We started by sending a minimum viable product (MVP) to 78 friends and family. We ourselves had the pain point, but we wanted to confirm others also craved the service."

  • The Follow Up by Nic Conley

    “If I were starting over and trying to grow strictly through organic social, I’d go with Instagram.

    Reels are super shareable, and people tend to check out your profile page more than any other platform.“

  • Raising Empowered Kids by Adam Toren

    “Maintaining engagement is actually the most effective growth strategy."

👉 Do you want to reach 1,900 newsletter creators & enthusiasts?

That’s all for today. Thanks for reading, and hit reply if you have any comments.

See you on Sunday.

Ciler

*Disclaimer: Affiliate link. I only recommend resources/platforms that I genuinely find useful.

P.S. I’ve sent this week’s issue on Thursday instead of Wednesday since I’m experimenting with publishing days. I’m sorry if I caused any disappointment.

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