5 Painful Lessons I’ve Learned to Be a Happy, Successful Writer

Don’t Lose Sight of Your Dreams Because of Someone Else’s “Advice”

Photo by Aaron Burden on Unsplash

I haven’t written anything new on Medium for the better part of 2018. What I have published is mostly repurposed content, edited and tightened up with a different headline, image, and tagline.

When you see yourself as a content creator online, not providing new content for the better part of a year is problematic.

Sure, I’ve been refurbishing and republishing old posts, but those have been few-and-far between.

I know, I know, there’s a certain irony in telling you to avoid reading advice by giving you more advice to follow. But this is more of a cautionary tale I want to tell you to help you, if not to avoid, but at least to be more aware of your feelings and your mission to help keep your writing going in the right direction and staying on the correct course.

This has been because of a couple of reasons that I want to touch on with this post below. I hope you’ll find this post helpful as these lessons have been difficult and painful for me to learn, yet after uncovering them, I feel freer and more cemented in my purpose than ever before.

1) If You Follow What Everyone Tells You to Do, You Miss Out On What You Actually Want to Do

You hear it often, right? To succeed as a writer, you not only need an audience or a voice or a message worth hearing or an email list, but a worthy platform to share your ideas on.

Like many of you, I strove to accomplish all of the above things. However, I came to a couple realizations this past year: one of the biggest was when I realized I never started writing online to get better at blogging about writing.

I didn’t want to build an audience for the sake of building an audience, and I never really wanted to make money with my words, either — that was just a means to an end. I started writing and sharing my work online to get better at sharing my thoughts and conveying my ideas with others. I started writing online to start a conversation around my work.

Perhaps the biggest reason I started writing online was because I wanted to write books and works of art that would change the world, starting with my readers and spreading to others in a positive, beneficial, and inspirational way. By leaning towards creating courses and coaching and striving to make money off my writing, though, I feel in a sense I’ve lost my way. After realizing this, I fell into a kind of quiet depression in regards to my writing, and stopped writing every day until I found myself not creating any new pieces at all.

My purpose with writing was never to build an audience or make money with my work. My mission was to inspire people to follow their dreams and make the changes in their lives they needed to get unstuck and truly make a difference.

In the end, making money and blogging and building an audience wasn’t the main focus, it was just a way to hone towards my ultimate goal. And I lost my way so badly because I listened to others telling me what to do and how to do it constantly when reading and following the people and writers I admired online.

2) Your Journey Isn’t a Static Line — It’s Filled With Ups and Downs that We Don’t Talk Much About

When I started blogging and finally working up the courage to sharing my work online, I thought I was on the right track. And when I built up an email list of over 1000 people and a Medium base of 9,000 followers, I was convinced I’d finally made it.

I mistakenly thought my journey as a writer was to first became an internet sensation with thousands of adoring fans, so that I could then follow my dreams of working on my fiction novel and being a working artist and a thriving writer. I mixed up the two so much that I convinced myself what I wanted wasn’t actually what I wanted at all.

The worst part in all of this was when I finally realized earlier this year that I’ve been really unhappy for years chasing a dream I thought I wanted more than anything. It was better than sitting on my hands and doing nothing, sure, but it wasn’t what I wanted to be doing with my life. And that, I believe, was deeply rooted in my belief that when things got good, they would stay good.

I haven’t found that the case myself. I don’t wake up inspired most days. I don’t feel unstoppable most of the time. The little comfort and confidence I’ve found with honing my voice, improving my style, and sharing my work has come from becoming more of myself and shedding the belief that the popularized ideas of others are what’s best for me and that things should be great all the time.

Like I read once on here, if you don’t love the writing game and every aspect of sharing your work online, then you’re not a true writer anyways.

What gibberish advice, right?

That’s like you need to be working on your dream all the time in order to be successful. No, you actually need to take breaks.

Although many writers insist that their way is the right way, or that the journey is all ups after it’s downs, things don’t work that way.

It’s one thing to build your audience up on a site like Medium, but it’s another to admit to yourself that following your dream of being a writer is hard work, and most of the work it takes to get started and restarted everyday is the hardest part of the whole thing.

3) Most Advice is Bogus And We Rarely Need More: What We Need is Experience Which Can’t Be Taught

When you first start out on any journey, you begin to relish the idea of gathering as much advice as you possibly can to be the best you possibly can be.

You consume so many books and podcasts and blog posts and courses that you run the risk of information overload, but yet you constantly find yourself wanting to learn more and more.

That is, until one day, you start to read the same things over and over. Things like to be a great writer you need to start writing crap; things like you need to do an idea dump or journal or do ‘morning pages’ to free yourself up to do better work; things like you must buy courses to be successful or worse, that you must sell courses on information products in order to be a successful writer online.

The worst one I continue to come across is that you must be a writer-entrepreneur hybrid to be an astounding success, which is simply not true.

It’s one thing to test your ideas and gain an audience by blogging on sites like Medium, and it’s another to pursue your own dream. It’s one thing to write what you want to write and say the things you want to say, and it’s another to urge yourself to monetize your passion and build a successful business as a writer in order to live life in your own vein.

One thing I’ve come to realize is that that dream is not for me. It’s not what I want to do with my life and it’s not what I want to accomplish with the little time I do have everyday to write. I don’t want to be a entrepreneur or a writer-entrepreneur hybrid or even a freelancer. I want to be a writer, and I want to do it on my own terms as best as I can. That’s it.

4) We Need to Stop Vilifying the Day Job (Maybe Writing Professionally Isn’t Actually the Goal for Many of Us)

Yes, I want to be a writer. Yes, the best way for me to fulfill that dream is to keep a job I enjoy give me the mental and financial security I need so I can slowly work towards making my dream of releasing my first book a reality.

The truth is, I’m not passionate about blogging as an ultimate goal. I’m simply passionate about sharing my ideas and building a community around my words, and I believe writing a book is the best way for me to inspire others and convey that to the world.

I want to write books in the vein of Steven Pressfield. I want to create the next War of Art. I want to write sweeping works of fiction like James S.A. Corey’s The Expanse and Brandon Sanderson’s Stormlight Archive and Stephen King’s Dark Tower series. I want to write a work that is fit for readers and takes them away into my own private world, just for them. I want to entertain, inspire, and delight my readers.

Yes, in a sense, I want to be a jack-of-all-trades writer. I don’t just want to blog and write work designed to help writers. I don’t want to just create courses to sell to my readers. I want to entertain them too. Fiction is my first love, but I’ve grown to love blogging and non-fiction too. I think both have a place in this world, and I want to help facilitate my readers in both of those ways as best as I can.

Of course, knowing that I want to focus on writing books, I have to tighten my focus and scope a little bit. I can’t create as much as I once hoped to. I need to tighten the reins on editing and completing my work, much in the strategy that Jon Acuff espouses in his book Finish. I want to be a finisher. I also want to release complete works that I’m proud of and put in the work to do so.

Most of all, I don’t want to rush the process. I don’t want to churn out a formula just so I can charge someone else to learn it too. I want to finish what I’ve started and if I then feel comfortable to do so, to charge for those finished works and spread my work, my knowledge, and my imagination as far and as much as I can.

5) When You’re Lost, Take a Break to Rediscover Your Roots

Not blogging for so long has made me feel rusty, but it’s also giving me a clarity I don’t think I would’ve obtained otherwise. And I’m grateful and happy for all of the pain it’s giving me, because it’s led to a greater understanding and appreciation for the world I love in and to a deepening and stronger connection to those I love the most.

I don’t really crave to be a writer-entrepreneur. I am not Jeff Goins. However, I do want to make an impact, and I think I can still do that while holding down a day job and writing as much as I can in the margins between.

In the end, redefining your route will help you much more than drifting aimlessly forward will. Because it will stop you from working too hard on a goal you don’t want to achieve, to do work you don’t want to do in order to live a life you don’t want to live.

What Type of Writer Do You Want to Be?

In the end, accomplishing your greatest writing dreams will allow you to live a life true to yourself instead of the one others espouse for you. And the best way to do that can be reviewing your journey so far, and then committing to pivot and redefine your work where ever you need to, so you can live a life true to your wishes and help become the best ‘you’ you can be.

In the end, success is whatever you define it to be. Only you can set the rules to lay the groundwork for your success, and only you can do the work that’s necessary to become the writer you dream you to be.


Thank you for joining me on this journey. If you found the post helpful, could you hit the clap button below to help me spread the word?

Blake is a writer, dreamer, and caffeine lover who lives in Vancouver, BC. He loves inspiring other writers to share their unique gifts and spread their message to the world. If you’re struggling to find things to write, you can download a FREE copy of “The Bulletproof Writer’s Handbook: A Proven Guide to Conquer the Blank Page Forever” to accelerate your progress today.