25 Valuable Lessons from Seriously Successful Writers

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.

About the Author: Bryan Collins is a writing coach on a mission to teach you how to write. Get his free 12-week writing course and learn everything you need to know to become a writer today.