25 Valuable Lessons from Seriously Successful Writers

by Bryan Collins


Stop it.

Stop feeling sorry for yourself.

You might think your problems are special, unique, or impossible for anyone else to understand. But you know what?

As writers, we’re all struggling with the same basic problems.

You’re not the only one who doesn’t know what kind of writer to become.

You’re not the only one who spends hours tinkering with sentences – and still hates them.

And you’re not the only one who’ll do anything – clean the bathroom, service the car, even run a marathon – to avoid sitting your butt in that chair and doing the work.

Almost every writer faces problems like procrastination, perfectionism, and self-doubt at one time or another. Even the successful ones swimming in writing jobs.

But the feeling of being totally alone on your writer’s journey is insidious.

It gnaws at your confidence and weakens your resolve.

It causes talented writers to give up when all they need to do is keep going.

And that needs to stop right now …

Why Being a Writer Is Like Driving in the Dark Without a Map

Imagine the scene.

You’re driving along a deserted road.

You haven’t seen another car, another person, or even a road sign in hours.

The car’s old engine has been making a strange rattling sound since you left home, and each time you hit another pothole, you think it might drop right out.

Regardless, you push your fears aside, sit up straight in your seat, and keep driving.

Because while your destination is not on any map, others have told you it’s worth the journey.

But it’ll be dark soon, and the fuel gauge is straying dangerously close to empty …

The recently departed American historical author E.L. Doctorow once said:

“Writing is like driving at night in the fog. You can only see as far as your headlights, but you can make the whole trip that way.”

It’s a powerful metaphor, but if you’re anything like me, you hate feeling lost.

You can’t stand the sense that you might be on the wrong track, leaving a trail of misspent time and effort.

Like most writers, I longed for road markings, or helpful directions from someone who’d made the same journey before me.

That’s why I asked 25 top authors, bloggers, and entrepreneurs one simple question:

What was your greatest writing or creative challenge, and how did you overcome it?

This is what they said.

On… Getting the Words Down

1. Ryan Holiday – American author, writer, and marketer

Ryan Holiday

Every writer’s challenge is to figure out exactly what it is that they have to say, specifically what only they can say.

For me, that was a question that had to be answered more with living than with writing.

Going out and doing unusual things was how I ultimately answered it.

That’s what put me on my writing path today.

2. Joel Friedlander – Blogger, writer, publisher, designer, and writing coach

Joel Friedlander

The biggest challenge I’ve ever faced as a writer was writer’s block.

Although I wrote tons of “corporate” or business-oriented pieces, I felt I had no access to my own creative potential, I was just a journeyman, a wordsmith, someone who wrote to other people’s agendas.

The way I solved it was by signing up for a free-writing group.

In this setting, the instructor identified me as a “crushed creative” and showed me many free-writing techniques that would give me access to the unending stream of creativity that’s running all the time in my imagination.

Since that time I’ve never had a difficulty writing, and I built my blog on this ability to write quickly and effectively, in accordance with my own creative impulse.

3. Shawn Coyne – Editor, publisher, literary agent, and writer

Shawn Coyne

The biggest writing challenge for me is actually putting my bottom in the chair and beginning.

How I overcome it is to remember that every writer I’ve ever known has faced the same problem.

The book that really made me understand this general Resistance to doing the work necessary to create a piece of prose is one I acquired and edited years ago… Steven Pressfield’s The War of Art.

That book, to this day, lets me know I’m not alone while at the same time, it kicks me hard enough to get me in that chair and begin typing.

4. Joanna Penn – New York Times and USA Today Bestselling Thriller Author, speaker, and entrepreneur.

Joanna Penn

The biggest writing challenge continues to be actually sitting down to write.

Resistance, as Steven Pressfield calls it, will always find a siren song to call you away.

The only way to overcome it is through routine and habit. Sit your butt in the chair and reach whatever goal you have set – that may be a time period or a word count.

I put headphones on and listen to rain and thunderstorms on repeat – this repetition of sound helps me write in different physical places and drowns out the distractions.

5. Len Markidan – Blogger, marketer, and Fortune 500 productivity consultant

Len Markidan

The biggest challenge I’ve always faced has been actually getting words on the page.

I’m a born procrastinator (I even dedicate an entire site to how I’ve overcome this) and can almost always find something more appealing to do than whatever I’ve defined as “work.”

Over the years, I’ve realised that rather than addressing this problem through brute force, I could make my life much easier by building habits and systems around my own shortcomings.

One thing I do now, as soon as I sit down at my desk, is write a single sentence.

A simple, achievable goal that’s so easy, I’m not inclined to put it off for later.

That’s often the hardest part, and once I have one sentence on the page, the rest often flows freely.

6. Nick Loper– Blogger, entrepreneur, and coach

Nick Loper

For me, the biggest writing challenge is staring at the blank screen and feeling the pressure to create something awesome from nothing.

It sucks!

So what I’ve started doing to combat that is keeping a couple of “idea” files on hand where I store any potential blog post or future book idea.

I just use Google Docs on my computer and the built-in Notes app on my phone.

When I’m in need of inspiration, I’ll just browse through these files and pick the topic that sounds exciting.

On the writing side itself, I’ve found some success recently in outlining my work first, which I never used to do.

I find it helps organize my thoughts rather than just brain-dumping on the page, and actually makes the writing faster because it’s like filling-in-the-blanks instead of starting completely from scratch.

On … Being Productive

7. Sue Anne Dunlevie – Coach and mentor for bloggers

Sue Anne Dunlevie

As my blog became more popular over the last 12 months, my biggest challenge was to keep to my writing schedule.

Sure, it was easy to write for my blog when I didn’t have 100 emails a day and didn’t have 1-1 clients to coach.

Once I added on clients and had to take care of so many emails, I started neglecting my writing. Which is so ironic – I got into blogging because I love to write.

In the past 3+ years, that was the best part of my business.

I relish getting a fresh yellow pad and my favourite pink pen and sitting down to write.

That was my flow time – my relaxation time.

Then writing my blog post just became another to-do on my list. I wasn’t getting joy from it. It was a chore. I knew something had to change – and change quickly.

So I found a great blogging strategist, a blog writing coach, who got me back on track. Daniela Uslan has helped me find joy in writing once again.

She gently asks me the right questions about what I enjoy when writing and has even helped hold my feet to the fire in order to get me on a writing schedule that worked for me.

I’m so glad I found her.

Sometimes we all need a little help in order to face our challenges.

8. Adam Connell – Blogger, online entrepreneur, and marketer

Adam Connell

Staying productive while writing has been a big challenge for me.

While I’m still not as productive as I could be, certain changes I’ve made to how I start my day have had a huge impact.

I start each day with some meditation, organise my tasks then start writing a blog post that I’ve researched the afternoon before.

Then in the afternoon I do some research for my next post which I write the following morning.

That’s followed by any email, social or comment management for my blog.

I’ve found that I’m more creative in the mornings and I’m better at editing/researching later on in the day.

Leaving tasks like email till later on help me maintain focus on the project at hand.

9. Danny Iny – Founder of Firepole Marketing, and best-selling author

Danny Iny

The biggest writing challenge for me (and for a lot of writers, who probably don’t realize it!), is trying to do two things at once – because writing really has two steps to it: figuring out what ideas you want to share, in what order, and (2) choosing the words to express them.

Doing both at once makes the writing process *much* harder, and the solution is to write a detailed outline first, so that you can separate the two steps out. That’s done wonders for me, and for a lot of my students, too!

10. Jon Morrow – founder of Smart Blogger, and former editor of Copyblogger and KISSMetrics

jon morrow

My biggest challenge was relearning how to write after losing the use of my hands.

For me, writing was always highly tactile. I was able to get into a rhythm that I never really appreciated until my condition (muscular dystrophy) got so severe that I couldn’t really type anymore.

Thankfully, speech recognition software was taking off, so I was able to switch to Dragon Naturally Speaking and continue writing.

But it was a lot harder than I thought it would be. Writing by voice was an entirely different experience for me, and it took me a few months to get used to the rhythm and get my writing voice back.

Needless to say, I’m quite comfortable writing by voice now.

In the long run, I think it might’ve even made me a better writer than I was before.

It’s certainly faster.

11. David Allen – Author of Getting Things Done, and founder of the David Allen Company

David Allen

The biggest challenge I have about writing is creating a standard context, which I consistently access, to write, no matter what.

I still need to coach myself to create the time, space, and environment, and trust that the right writing will show up.

On … Self-Belief and Overcoming Perfectionism

12. Kevan Lee – Content Crafter, Buffer

Kevan Lee

I like things to be perfect when I publish them.

Personally, I sense this stems from my placing a certain amount of self-worth or ego in the content that I publish, which is something I’m continually keen to improve on. My challenge can be to simply hit Publish, to ship things, when I’d prefer to hold them tight until they are flawless.

“Perfect is the enemy of good” is something I think of often, and while I definitely feel there’s a place for perfection (and the pursuit of perfection), what’s been useful for me is embracing this idea of shipping early, putting your work out there and receiving feedback, and having the courage to create.

Doing it often has helped me overcome my fears, working with a deadline helps too. And the more I do things this way, the more I realize that the small imperfections that I’ve noticed often go unnoticed by others. All this really helps reinforce the great benefits of sharing your work, early and often.

13. Pat Flynn – Blogger, entrepreneur, podcaster, and writer

Pat Flynn

The writing of the first draft of my new book was a struggle for me because I wanted it to be perfect.

That first draft is really important I’ve learned through reading books like Bird by Bird by Anne Lamott and just hearing and getting advice from several other authors out there that you just have to write.

Some people actually take their delete key off their keyboard to force themselves not to be able to actually delete and get into edit mode.

You have to be in just creative mode, which is definitely the opposite of edit mode.

Then I decided, okay, I’ve been big on podcasting. I use my voice a lot.

I’m just doing a brain dump in this first draft, why don’t I just talk it out and have it recorded and then have somebody transcribe that and have that become the first draft.

That’s what I did. I was able to, in about two and a half weeks, finish my first draft of my book which is really cool.

14. Steve Scott – Blogger, nonfiction writer, Kindle publishing, and habit change expert

Steve Scott

One of the biggest writing challenges I have faced in the past, and still face today, is perfectionism.

First there is a desire to always do better. The feeling that while what you write may be good, there must be some way to make it better.

Second there is the self-doubt that creeps in over time. More than once I have read something I wrote months before and just think it is awful.

Perfectionism is something that most authors face and must learn to combat.

There are a few methods I use to combat perfectionism.

  1. Good is good enough. Nothing you write will likely be perfect. Once you feel that what you write is good enough, ship it!
  2. Write often. Writing is a habit that should be done every day. You do not need to write 8 hours daily, writing that much may actually be counterproductive, but an hour or two each day is important. When you write this much, your work will seem better, because it will be better.
  3. Don’t be too “wordy”. I think the best writing is direct and to the point. You do not need a lot of flowery accoutrements in your writing. While editing, simplify your writing. With simple writing it is easier to decide if the point you have made is clear.
  4. Write first, revise later. Write a terrible draft, give it some time and go back and edit as a separate process. Genius is not in the writing, but in good solid editing. When you do good edits, you can let go of the need to make it “even better” because it should be really good.
  5. Send it to a professional editor. I outline. I write. I edit. THEN I send my work off to be edited again by a professional I respect. With two solid edits you can feel secure anything you write is “good enough”.
  6. Don’t take yourself too seriously. I don’t think I am writing Shakespeare or that I am the next Ernest Hemingway. I hope my books make a good impact on people’s lives, but I do not try to think that they need to be “revolutionary” or “life changing”. All I hope for is to make them enjoyable and something that people will perhaps learn something from. Keep your ego in check when writing. The writing is not about you, it is about what you can do for others.

15. Bryan Hutchinson – Author, blogger and founder of Positive Writer

Bryan Hutchinson

The biggest writing challenge I ever faced was myself.

The belief that I wasn’t good enough and the extreme skepticism that I could write work that others would want to read.

In short, I doubted myself. It was debilitating and for years I didn’t write because of it.

Overcoming doubt wasn’t easy.

It took years.

I wrote in a private journal and I started blogs that I shared with only a few people in my circle of trust.

Over the years as I continued to write, and slowly, but surely, shared my work with more and more people, my confidence began to increase.

Of course, there’s much more to the story than that, but ultimately, the key to overcoming doubt for me was actually writing for myself and eventually sharing my work with those who I knew cared about me and what I was writing about.

As my confidence increased I shared my work with more and more people.

16. Henneke – Copywriter, Author, Marketer, and Writing Coach


The biggest writing challenge I’ve faced is starting my blog. I didn’t see myself as a writer. I didn’t think I could blog. I had no confidence.

But I desperately wanted to leave my corporate job, so I needed a way out.

How did I overcome my self-doubt?

I took Jon Morrow’s guest blogging course, and the main thing I learned was that writing isn’t magic. You can learn how to apply writing techniques to make your content engaging, persuasive, and inspirational. I read a pile of copywriting books.

I started to study blog posts and analyzed what kept me reading on and when my mind started wandering off. With hard work and determination, most people can learn how to write well.

Now, I coach others to become better writers, and I’m not even a native English speaker. If you’d told me that two or three years ago, I would have said you’re crazy.

On … The Craft of Writing

17. Johnny B. Truant– Indie author, blogger, and podcaster

Johnny B. Truant

Back when we started the Self Publishing Podcast, I was supposed to join Sean and Dave on the show as the “everyman” writer because I’d only written one book and couldn’t manage to complete a second – despite years of trying.

The problem at the time was that my characters never really did anything. They just kind of stood around and talked.

Even when I added action, the action never went anywhere. Working with Sean and Dave helped me see that although I thought I was a “pure pantser” (making things up as I went along), I actually worked much better as something between a “pantser” and a “plotter.”

Today, Sean and I work using “story beats,” where we roughly map out the main points of what will happen and I figure out the details between them as I go.

That hybrid approach has changed me from a writer who couldn’t finish a second book to one who now publishes 1.5 million words (about 1 1/2 times the full Harry Potter series) per year.

18. Gregory Ciotti  – Lead Content Strategist and Writer for Help Scout

Gregory Ciotti

The greatest challenge I’ve faced is the temptation to impress. Writers are traffickers of wit and wisdom, and we want so badly to leave lasting impressions. But in trying to prove ourselves we can end up being selfish. I’ve always been fond of this quote from Harvard psychologist Steven Pinker: “Bad writers don’t point to something in the world but are self-conscious about not seeming naïve about the pitfalls of their own enterprise.”

To overcome this anxiety, write for an audience of one. A single person. Not a “persona,” by the way, a real person. I’ve found having someone in mind creates a desire to serve. You’ll care less about impressing a faceless audience and care more about solving the problems of someone in need.

19. Mary Jaksch – Author and Editor of Write To Done

Mary Jaksch

My biggest writing challenge was starting to write for an online audience. When I started blogging, I was already a published author and my book, Learn to Love, was published in 7 different languages.

Just before starting my first blog, I had come back from a trip to Brazil. My book had just been translated into Portuguese and I felt proud to see a huge pile of my book displayed in bookstore at Rio de Janeiro airport.

As you can imagine, I felt pretty confident about my writing when I started to blog. I thought, ‘ Well, this blogging thing is technically challenging, but at least I know how to write!”

How wrong can you be…

When I finally published my first posts, I was in for a shock. First of all, nobody read my posts. In fact, for three months I only had two subscribers, my son Sebastian and my best friend Birgit. I was so desperate that I subscribed my cat, Sweetie – just to get up to three subscribers!

And when readers finally found me, they didn’t like my way of writing.  It was demoralizing…

Really, the style of writing I had developed when writing my book didn’t work at all online. I used long, complex paragraphs and had a preachy undertone that put off potential subscribers.

When I finally admitted that I had to change the way I wrote, I started studying all the research I could find about the way people read online. And then I adapted my style accordingly.

It took me a whole year to recalibrate my style of writing. These days, my mission is to help people become influencers and outstanding online writers. As an example, here is a post about how to evoke emotions in your writing.

20. Tim Brownson – Life coach, and blogger

Tim Brownson

My biggest challenge was rushing to publish. I never write a blog post before I need it and sometimes I’d be so excited I’d publish without editing properly.

I think after the 20th complaint that a blind monkey on acid would make fewer typos I realized I needed to take editing a tad more seriously or lose readers.

One of the best bits of advice I was given was to read each post out loud after editing as it will often highlight mistakes that the brain has ignored when reading. I still make mistakes, but probably about 5% of what I used to do.

21. Carol Tice – Freelance writer, author, and blogger at Make A Living Writing

Carol Tice

One big one came early in my career, when I got my first shot at writing a long feature.

It was an expose on a right-wing group that had recently come to Los Angeles, and a woman who infiltrated their organization. I had a ton of amazing information, and my first draft for this 3000-word assignment was about twice as long!

I had no idea how I would cut it down. I was drowning. So the only thing to do was — get help.

I started with a writer friend who wrote for TV and had written a nonfiction book. I’ll never forget the advice she gave me about using active, present-tense verbs instead of passive ones — once I turned “had been going to the store” into “went to the store” throughout, that alone cut some serious word count!

I think it was 5,000 words when I brought it to my editor and basically said, “Help!” He read it, and gave me a road-map of how to shrink it down, what could be cut entirely, what could be said more succinctly and how. I’ll always be grateful. The final story was optioned for a movie — twice — and I ended up making over $20,000 from it.

Even better, I learned to ask questions of editors, and ask for help if you need it, an approach that’s served me well with all sorts of writing clients. It’s also the approach I used working with Jon to write my first guest post for Copyblogger — on his advice, we actually tossed out the first draft completely and I wrote an entirely new idea for the first post with his guidance. It ended up in Best of Copyblogger for that year.

On … The Business of Writing

22. James Chartrand – Blogger, copywriter, and founder of Men with Pens and Damn Fine Words

James Chartrand

One might actually suggest that writing itself is the biggest challenge – and the only way to overcome it is by writing.

But that’s getting philosophical, and I digress.

I’ve probably touched on every writing challenge that exists, at some time or another.

Writer’s block, apathy, disillusionment, comparison bias… but I don’t hang onto those for long.

They’re all luxuries that can’t coexist in a business environment.

If you want to succeed, if you want to make money, you need to get over yourself and get on with the writing work.

My most recent “luxury” was apathy towards my blog – I hadn’t written for it in a long time because I was bored with the topic, disengaged with my audience and feeling like I’d said it all.

So I decided to go back through older posts and rework them completely, applying what I know today to make them so much better.

The exercise helped me get back to my roots, revisit the enjoyment I used to feel about blogging and sparked my interest in writing about new and related topics.

It worked so well that I recommend this to everyone, actually, and you can read more about it here.

23. Demian Farnworth – Chief copywriter for Copyblogger Media

Demian Farnworth

Finding my way out of ghostwriting.

When I got my start as a freelancer I discovered that ghostwriting work was abundant.

I took it in by the loads. But I also discovered I hated doing it. Though I made decent money from it, I couldn’t stand the fact that someone else was getting credit for it.

I learned that side of the business wasn’t for me, so as the work dried up, I didn’t take any new ghostwriting work on.

Instead, I started marketing myself as a professional writer for hire — someone who could help elevate the visibility of a company while still keeping his byline. I’m fortunate to be able to do that at Copyblogger.

24. Tom Evans – Writer, author’s mentor, and teacher of mindfulness

Tom Evans

My biggest writing challenge has always been promotion of a book once it’s been written.

Writers can be quite self-effacing, shy and retiring kind of creatures and I fall into that category.

To date, my approach to marketing a book has been to write another one and another one, in the vain hope the latest book will somehow magically up sell the ones before. With my latest two books, I have taken a new approach.

I love writing, and creative endeavours in general, and this is why I’ve got stuck into writing another book as opposed to selling and promoting the one I had just finished.

So what I’ve done with my latest two books is to channel my creativity at their marketing.

This then doesn’t make it either as scary or boring.

So what does my new world look like?

Well, I have my own podcast show, called The Zone Show, based on the last book but one, called The Zone. This has been the best networking tool ever.

I get to reach the tribes of my guests and many guests have their own shows and interview me in return.

My latest book, New Magic for a New Era, is the progenitor of a huge spin off industry. I am half way through creation of a self-study product to augment each chapter.

Each product I release creates more buzz for the book as well as more revenue. The whole result has been a spiral of creativity and sales.

This in turn has created a nice flow of passive income which by summer will give me enough income so I can get back to writing again without worrying about where the money is coming from.

25. Hugh C. Howey – Best-selling author of the “Molly Fyde” and “Wool” sagas

Hugh C. Howey

My biggest writing challenge was learning to write with an expectant audience.

It was so much easier to write my first five novels, back when the only people waiting with bated breath were my partner and my mom.

When I suddenly had tens of thousands and then millions of readers waiting on the next release, I became a lot more self-critical and a lot less self-confident.

The quality of my writing went down as I began trying too hard.

There were a few weeks where I deleted everything I wrote.

This caused me to panic, and I had to remind myself that I was just writing the stories I wanted to write, that I didn’t have to please anyone but myself, that no one would read any of this other than my mom.

And my mom would always be proud.

Most of the challenges of writing have come with success, which is to say that they are great problems to have.

How to balance writing time with other demands. How to have a balanced family life with travel.

How to manage finances when income fluctuates. How to keep expectations realistic, enjoy the moment, but know that it is never meant to last.

It can be a rollercoaster, watching an entertainment career take off. But I wouldn’t miss it for the world.

Just a Little Further, You’re Almost There …

As a writer, realizing you’ve only got a vague idea of where you’re going or wondering if you’re going to reach your destination any time soon is never pleasant.

This roundup post has uncovered the challenges experienced writers faced on their individual creative journeys and revealed the solutions they found.

All of the interviewees have dealt with failures and successes of all types over the years, and they’re still going. They’ve overcome problems we can all empathize with.

If you’re struggling with your craft, and a solution isn’t in sight, don’t take this as a sign that you should put down your pen, turn around, and go home.

Instead, the next time you encounter a problem, use the 25 solutions in this post as directions for your creative journey.

You just have to be brave enough to keep going.

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Bryan Collins


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Written by Bryan Collins

102 thoughts on “25 Valuable Lessons from Seriously Successful Writers”

  1. Hey Bryan,

    This was a great post. One interesting thing you shared was what Kevan Lee and a few others shared. Perfectionism. That’s a curse if I ever saw one … and it’s one that I’m cursed with from time to time and continue to work on to improve.

    But I loved what Bryan Hutchinson said. My biggest obstacle is myself. I push myself too much and take on so many things that I quickly get burned out. And if it’s not that, I fall for the perfectionist bug.

    Also, with that, I also had doubt in the things I would write about. And had to learn how to get confidence in what I write.

    Excellent post here, Bryan.

    – Andrew

    • Hi Andrew,
      I do agree with you on all you have mentioned above. Am working hard to just do to avoid perfection in my work. Another I see is distraction for my surrounding which is in my control.

      Well am inspired by this post not to give up. Great post I agree. I will share this post with my followers.


  2. Hard to understand how you can find only white writers. Nineteen of your writers are male. Six are women. No people of color. How is this inclusive or representative of the world of great writers? Much of the advice feels similar, and I suggest earnestly seeking out different kinds of voices to yield a wider breadth of responses.

    • Hi Michele,

      Thanks for your comment, which is well-taken. Speaking as the blog’s managing editor, the oversight is entirely mine and all I can say is that the lack of diversity certainly wasn’t intentional.

      On reflection, we should have ensured that there was more balance in the selection of writers at the outreach stage and will make sure to do so in future.

      In case it’s at all reassuring, this previous “roundup” post enjoyed a more representative mix of people:


      And to your point about participants giving similar advice, I think it just demonstrates that many writers do struggle with the same kinds of issues, regardless of success level.



      • You don’t need to defend yourself Glen.

        Enough people know you, and in particular Jon, to know there was no malicious intent.

        People are just looking to be offended. Sometimes things just pan out like this.

        Next time however, I expect a Muslim writer, at least one gay writer. India and China should be heavily represented as they make up a third of the worlds population and a lot live in this country and there should be at least one Donald Trump supporter. Fortunately for you, you hit the bald, pasty Limey minority otherwise I’d be up in arms.

    • Gimme a break Michelle. These people are quite obviously writers that have Bryan’s respect and admiration. It’s a good article end of story and he’s entitled (and so are the editors) to publish what they like without second guessing who they might offend. Especially given that there’s no offensive comments in the post, only helpful information, even given the fact some of it might be repetitive. Over political correctness destroys good opinion and commentary, so with all due respect lets just get over it…

  3. Firstly, It’s amazing to be including with such luminaries, so thanks Bryan!

    I can so resonate with those that say starting is the hardest part. I wasn’t asked that question, but I think when it comes to getting the words down, it’s a question of just starting knowing that the first draft will probably suck anyway. Therefore, it gives you a great chance to do some serious rewriting.

    As the quote goes (which seems to have been attributed to just about everybody from Douglas Adams to Michael Crichton) – “good books aren’t written, they are rewritten”

    Well to paraphrase – good blog posts aren’t written, they are rewritten.

    • Great to include you! I read somewhere that if you’re procrastinating spend just five minutes working on the task at hand. Often that’s enough to get the ball rolling. I too read my post out-loud before publishing.

  4. This is a cool list, Bryan. I have a request. Can you include me on future lists, please? I am a freelance writer, blogger and self-published author. Let’s chat when you’re available.

  5. Very nice tips by the expert bloggers and I see that most of them face the same problems, while writing, as I do. I agree developing habits and rituals are the best ways to overcome the inertia and procrastination.

    • Hi Cathy,
      I try to write between 06.00 and 07.30 every morning. This habit makes it easier for me to hit 1,000 words a day, every day. Before this I used to write at all different times or not at all. The power of small wins is a great way to grow as a writer.

  6. Terrific roundup, Bryan. It’s always encouraging to hear other people struggling with (and getting around) the same issues you face yourself. This is a terrific group of writers you’ve assembled.

  7. Hello Bryan,

    Thank you for this inspiring list of challenges so many admirable writers face but, the important part, they overcome. I shall keep this post and refer whenever I fall into one of these silly traps.

    Quite moved to see Sue Anne admitting to having struggled to find time to write – she is so brilliant and exemplary in thanking kindly all those who comment on her blog and does so promptly.

    So, thank you again, Bryan – congratulations on being here and in Writers Village.


  8. Hi Bryan,
    really awesome list you’ve got here. Being a newbie in blogging, I find that i struggle with the desire to impress my online audience, so when you add self-doubt, perfectionism and trying to write productively with 2 kids under 2, then u almost have the perfect recipe for ‘not-writing’. ?
    Anyway, I signed for Jon Morrow’s Serious Bloggers Only, and Its been a blast.
    This Stay-at-home mom will surely bring the house down!
    Have a great day.

  9. Thank you for this inspiring list of challenges so many admirable writers face but, the important part, they overcome. I shall keep this post and refer whenever I fall into one of these silly traps.

  10. I’m really inspired Bryan,
    What a heart warming round up. I must confess that this is one of the best posts I’ve read this yea.

    My own biggest challange is coming up with blog post ideas. I’ve trained myself to be waking up early in the morning to write and i usually wake as early as 4am but most times, I’ll end up just staring on my screen and being confused of what to do and where to start from. And before you know it, I’ll end up not writing even a single word.

    I’m always trying to figure out how I can overcome this because I’m no longer finding it funny at all.

    I’m going to put some of the tips mentioned here into practice and see what impact it will create hopefully, I’ll be able to overcome this challange.

    How do you usually come up with the ideas of what to write?

    Thanks for sharing Bryan, really educating :).

    • Hi Theodore,
      If you’re having trouble coming up with ideas, try down 5-10 ideas every day. It doesn’t matter if they’re good or bad. The point is to build your creative muscle and get into the habit of coming up with ideas regularly.

      If you have active readers ask them ‘What are you struggling with right now?’ and then do you best to solve these problems for your readers in your blog posts.

  11. I enjoyed this post because it goes to show that even the people you look up to as greats have the same struggles as you do. You would never think that they too struggle with coming up with what to write, or not wanting to put something out because it’s not “perfect.” When you hear other writers stories, it really makes you get over yourself, stop complaining, and just write.

  12. Bryan — nice to see you here again!

    Great presentation on this roundup. James Chartrand is one of my favorites. Apathy and comparison can’t coexist in a business environment. Love that! What a great suggestion to reconnect with your audience by revisiting topics you’ve written.

    Sometimes I fool myself into thinking that I can take a “free pass” from writing for awhile and it won’t have any effect on my relationship with my blog. But it does! Apathy’s a little bit like mildew. You don’t mean to invite it in. But if you don’t stay vigilant, it just moves in to stay.

    Thanks for the wake-up call. 🙂 I know lots of others who’d appreciate one too, so I’m off to Tweet it out and share.

    Have a great weekend!

  13. Hi, Bryan,

    It’s an honor to be included here with some of my favorite bloggers and writers.

    I have found that Jon’s Guest Blogging course, as well as the Serious Bloggers Only mini-classes and forum, have helped me stay focused on writing specifically to get readers and subscribers to my blog.


  14. Bookmarked!

    I love the night driving analogy, really inspiring. It feels good to know we’re not alone in this position. The most common challenge is to sit down and write. So much research, so little on the page!

    Thanks for the inspirational article!

    Heitem Ak

  15. I can resonate to a lot of these entries. Recently I was talking to a young man who had a day job in something tech. He wanted to get into writing to be creative. I wondered if I should warn him, “When you write for money, it’s about process and structure (as Henneke says), not creativity. You’ve got to make something out of nothing almost every time (as Nick Loper says) and find time to fit everything in when you become more successful (as Sue Ann Dunlevie says).

    But I figured, why not? He’ll either adapt to a new view of writing or decide to do something more creative, like truck driving. 😉

    • Blogging sometimes is a curious combination of the technical and the creative. Lots of bloggers complain the find the technical parts of blogging a challenge.

      Your friend could also consider technical writing and slowly transition from there.

  16. I have the advantage of reading these posts pre-publication. So, yesterday I’m reading along, nodding my head in agreement, reminded that most struggles are not unique or even worthy of the time it takes to throw a decent pity party.

    And then, this by Tim Brownson:

    I think after the 20th complaint that a blind monkey on acid would make fewer typos I realized I needed to take editing a tad more seriously or lose readers.

    I spent the next 10 minutes wiping coffee off my keyboard.

    Too funny.

  17. Hey, Bryan-

    This is an insight into the ‘community of bloggers’ thing I’ve been reading about. I read your article over at the Writer’s Village the other day. It’s like running errands and seeing your neighbor at the store.

    I can relate to many of these writers’ challenges. It’s another ‘saver’ to refer to when you’re not sure what the next step is. I’m working on a couple of ebooks, with the help of Steve’s publishing ebooks for Kindle, introduced to me courtesy of Sue (community again), and I’m writing a memoir. I checked out memoirs from the library, because I believe in learning a craft from people who’ve done it already.

    My writing improved immensely after I read Jon’s post on editing a few months ago, and studied the way he writes for an online audience. It was a wake up call for a vain writer. I had no idea I was being so wordy, so long-winded, so unnecessarily verbose, so… (you get the picture). Enjoyed both the posts, by the way!

    • Hi Gigi.
      It’s nice to get positive feedback. I spent a lot of time on both posts (more than I’d like to admit 😉

      Yes blogging is a community and it took me a while to figure that out, but here’s the thing:

      Advice from the community can help you grow as a writer and expand your audience. The more you give, the more you get out of it.

  18. Hi Bryan,
    Thank you for your article. I liked the format–you stated the common writing problem in the box, and then underneath explained the solutions to it. I haven’t had writers block yet after blogging for almost a year. I keep waiting for it to strike like waiting for the other shoe to drop. Thanks for the post for if/when it hits me.

  19. Great post! Love to see how many notable writers experience the same challenges I do. It makes me feel better! Such good tips on overcoming them; I’m bookmarking this post right away! Thanks, Bryan!

  20. 1) The only writer who has writing block is a writer who doesn’t have a deadline.
    2) Inspiration comes from putting the seat of your pants on the seat of the chair.
    3) Get a copy of Stephen King’s book, “On Writing.”
    4) Only write if you can’t help it.

    There you go, from two people who have had over forty books published since 1978. It’s not a steady-income life, but it’s the life you must choose if it calls you.
    Best — Meredith and Win Blevins

  21. Hey Bryan,
    Great post Bryan. I hadn’t think that such a great writers had some challenges in their writing, and how they overcome those challenges is very helpful to me to learn from them.
    Thank you very much Bryan.

  22. Thank you Bryan for an informative post that also inspires. I loved the quote from Jon Morrow. His story shows us how writing high quality copy is possible under all circumstances. Great job.

  23. One great example of this is Ramit Sethi. His blog, I Will Teach You To Be Rich, has a regular output of highly engaging, personal, image-rich, and information-packed articles. Although Ramit writes from a first-person perspective, he openly acknowledges that a lot of people have a role in enhancing the content.

  24. Hi Bryan, What a great post.
    I agree with James Chartrand that writers’ block and empathy etc. are luxuries. We have to do what ought to be done.
    I believe in writing rough drafts without editing. I just let the ideas flow and bother about editing later on.

    • Thanks. Some writers actually go as far as removing the delete button from their keyboards so they can get that first draft out of their head and onto the blank page with stopping to edit.

  25. Great post, I’m so glad to see that some of the great writers also struggled with the same things I do. The biggest culprit being perfectionism. You don’t want to know how many drafts I have that I didn’t publish because they are not perfect enough.
    I must admit, halfway through, I checked again to see how many valuable lessons, because I saw myself in the first 10 already and reading further, more of myself, but it seems to accommodate some negative people there had to be more than 25 😉
    I love writing, but hate editing!
    And you don’t want to know how long it took me to leave this comment, because of reading it through to check that it is PERFECT!

    • Hi Linda,
      If you love writing but hate editing considering hiring an editor to review some of your work. You can get one to review a 15,000 word novella for as a little as EUR200. Alternatively, you could ‘barter’ your writing services with another writer who can edit your work.

      • Yes, Bryan, I think that will be the best solution for me. Thank you. (Glad to see your post is “making headlines”.

  26. Hello Bryan,

    Mindblowing round up post and it hit home. I personally face quite a few writing challenges. I could relate to #14, #16, #18.

    Procrastinated over starting a blog. I know I had to know everything about what blogging entails to start a blog. I was wrong!

    I started my blog a little more than a year ago. The first six months were insane. I doubted myself, faced a lot of challenges but happy to kept going. At this stage I am aware I have bucket loads to learn but as they say you have to be in it to win it. So here I am blogging and learning at the same time from awesome bloggers like you, Jon Morrow who never fails to inspire, my blogging mentor Harleena Singh.

    This is a post many bloggers would love as there’s a clear cut message that even as an expert one can face challenges. The secret is to find the solution that works for us and not allowing our shorcomings to ruin our dreams as a writer.

    Truly motivated. Thank you for such a great post. Wishing you a wonderful weekend:)

    • Hi Hema,
      Thanks for the high praise 🙂

      It’s natural to doubt yourself. One way to get over this is to keep a list of affirmations that you read from time to time. Then when you are doubting yourself you can read this affirmations and remind yourself why you do what you do. I also recommend reading the War of Art by Steven Pressfield.

  27. Wow this is very inspirational Bryan, I needed this! Its always great to read about how successful people struggle to succeed, it gives us hope hearing how they get through those obstacles. I won’t procrastinate to write now 😀

  28. Like any other competitive field, it’s about discipline. Sitting down to write the things I want to write, after writing a few thousands words of writing down what I’m paid to write. Good to know I’m not the only one who struggles.

    Here’s my quote for you to include on the page in a couple years when I’m famous: “Writing is like making a sandwich: If all you do is talk about it, you’re going to starve to death.”

    Fun read!

  29. Thanks for the huge post, Bryan.

    You and the group you gathered touch on most everything difficult about writing and getting read. And you made it look easy.

    My favorite part, aside from the advice, is seeing how everyone represents themselves online. So much variety from so many stars that you can’t go wrong with any of them.

    Add the writers to the commenters and you’ve got enough pages gathered in one place to review for a week. Great fun.


  30. Thank you, Bryan. Because writing’s mostly self-driven, sounds like the biggest challenge everyone has is themselves. Even with super-successful writers, finding the time, confidence and discipline to put words down isn’t easy. Now I don’t feel so bad! And as always, Jon Morrow is courageous and inspiring.

    • Hi Laurie,
      That’s good to hear. Finding time can be a challenge which is why I like to write first thing. As for confidence? Well that comes with practice and with accepting that it’s natural to be unsure about your work from time to time.

  31. Great article as usual. I get a bunch of email everyday from top of the line marketers like Seth Godin and Dan Kennedy and this blog is always the first one I go to .

    My biggest challenge is wondering if the niche I’m in is profitable enough. (Which relates to your driving in the dark analogy.) I’m trying to specialize in my copywriting, but I’m never sure if there’s a big enough group to cater to. I’ve tried to do research on this, but the findings are so thin, I’m not sure if I’m in the right zone or not.

    Anyway, that’s my biggest pain. Thanks for the great post.

    God Bless,


    • Hi Mark,
      You’ll find lots of great posts here that will help you narrow your niche and make a profit. My advice is to write strategic evergreen posts and build your email list. I hope this helps.

  32. Bryan,

    What an excellent round up post. I also love the graphic design work in the post showing the author’s photo and quote.

    It was great to see writers I knew (e.g. Ryan Holiday and Carol Tice) and several new writers (e.g. Tom Evans).

    And that reminds me, I have some more writing to do today!

  33. Interesting to see that on any writing blog, the most popular topics are posts against procrastination, how to find ideas and how to just simply get things done. I definitely have struggled with some of these problems as well, especially with perfectionism.

    Perfectionism is really just fear… fear of not being enough (of a writer). You don’t want to damage that carefully constructed image you have of yourself, the great writer. The paradox is, as longh as you are not ready to risk your self-image, that great writer will never come into existence.

    The only way to go is really just to push through the fear and do it.

    Great post – congrats, Bryan!

    • Hi Alex,
      I agree, perfectionism is another form of fear and it’s a deceptive one. If you don’t ship because it’s not perfect you will never really get what you need to become a better writer.

  34. Thanks for an interesting article. It’s equally interesting that out of 25 great writers, there are only 6 women. My guess is that the male-female ratio of writers is closer to 50-50. This isn’t a criticism of your post, more a reflexion on which gender gets recognition in this and other industries… James Chartrain already made the same observation when choosing her pen name.

    • Hi Isabelle,
      I contacted about 150 people for the post. Some of the other female writers who replied focus on fiction over blogging, and I’ll be sharing their answers on my blog soon.

      James wrote a post about her experiences as a female writer and blogger on Copyblogger. It’s a great read.

      Thanks for reading.

  35. You guys are really an inspiration. I have two blogs I bought the domain the same day. Today made it seven months since I bought them. I have worked successfully on one to certain extent but the second is yet to kick off. I just don’t know why. My biggest challenge I must say is me starting the blog.

    • Hi James,
      There’s loads of great advice here about how to start a blog and what to do once it’s up and running. My personal recommendation is to build your blog’s audience by writing guest posts for people in your niche.

  36. Really awesome list you’ve got here. Being a newbie in blogging, I find that i struggle with the desire to impress my online audience, Thank you, Bryan. Because writing’s mostly self-driven, sounds like the biggest challenge everyone has is themselves. Even with super-successful writers, finding the time, confidence and discipline to put words down isn’t easy. Now I don’t feel so bad! And as always, Jon Morrow is courageous and inspiring.

    • Hi Solanki,
      Find the time and confidence to write is a common challenge. I recommend reading the book the War of Art by Steven Pressfield. He tackles both topics in an accessible and motivating way.

  37. This article was exactly what I needed right now. I’m working on a story that just won’t cooperate with me. Thanks so much for the tips. Definitely saving this for later.


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