The 7 Biggest Challenges Newsletter Creators Face

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

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

“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.”

“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.”

“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.”

“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.”

“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.”

“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.”

“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.”

“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!”

“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!”

“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.”

“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.”

“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.”

“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.).” 

“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.”

“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.”

“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.”

“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.”

“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!”

“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.”

“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.“

“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.”

“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 :)”

“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.”

“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.”

“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.”

“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.”

“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”

“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.“

“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.”

“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.”

“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.”

“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.”

“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.”