The modern digital writer. Image via Midjourney.
Regardless where you are on your online writing journey, they can do the same for you
I’ve been writing occasionally online since there was an online, starting my first blog combining my expertise in tennis and strategy way back to 1997.
But I could never write consistently.
As a busy husband and father with a demanding full-time job, the best I could manage was an occasional blog post once every few months to once every few years.
It seemed like my online writing career was pretty much over.
What can I add to the conversation?
Fast forward to 2024 and you’re reading my 68th article.
As of this writing, I now have over 3700 followers on LinkedIn, over 1400 on Medium, over 700 on Twitter, and over 220 Substack email subscribers.
I don’t share these numbers to brag, but to share what’s possible.
But the biggest change is that I love and look forward to writing alongside my 9–5 — I’m literally excited to sit down and write every day, either before work, or on nights and weekends.
And I’m part of a vibrant, supportive community led by leading creators in the space.
How did I do it?
I’ll lay out my biggest learnings along the way.
The path to a consistent writing practice
I was fortunate at the beginning of my writing journey to Dickie Bush and Nicolas Cole’s Ship30 for 30 writing challenge, and later their Captain’s Table Alumni group.
While this helped me get traction throughout 2022–2023, things went to a whole new level in late 2023 when I started working with Tim Denning and Todd Brison as part of their Write 4/28 Challenge.
Finally, I had grown enough to be able to commit to and successfully complete all 28 days of their 4/28 writing challenge, writing through major work projects, family travel, and the Thanksgiving holiday.
I’ve since graduated to Tim and Todd’s “Badassery Mastermind” group, and am learning more every day.
My top five
Over this time, I’ve crystalized my end-to-end writing workflow, and kicked things into high gear.
Along the way, I’ve condensed 5 dead-simple ideas that continue to have an outsize impact on both my writing and my reach:
#1. Write and Ship Something Small Every Day
#2. Never Start with a blank page
#3. Be willing to invest in yourself and your writing
#4. Community is the heart & soul of writing
#5. Access Flow States
#1. Write and Ship Something Small Every Day
“Real artists ship”
– Steve Jobs
I used to think writing was all that mattered. So I just wrote. For hours. in isolation.
For a stretch, I simply had a goal of writing for 20 minutes a day without stopping, either in a Google doc, or in my journal.
And while that was therapeutic at some level, all I ended up doing was amassing thousands of words that connected with no one and went nowhere.
Everything I wrote stayed locked away in places no one could ever read.
Learning a daily shipping habit
My writing completely changed when I learned the importance of posting tiny idea fragments to X and LinkedIn on a daily basis from Dickie and Cole.
I was also heavily influenced by the client-centric nature of Design Thinking and Roger L. Martin’s “Playing to Win” strategy framework, as well as the concept of Continuous Product Discovery.
When I started applying these practices to my own writing, I set in motion the biggest shifts yet.
Why do I write?
I realized my goal with my writing was to connect with like-minded readers and help them solve the problems I’d solved, applying some of the interest and expertise I’d amassed over the past 20+ years.
Writing didn’t have to be a solitary “diversion” going nowhere –
I could now start connecting with an audience interested to read and share what I had to say.
Data-Informed Digital Writing
Instead of investing weeks writing many thousands of words, I could quickly jot down a few bullets of an idea and immediately get feedback.
This would quickly give me a sense of what people were interested in, and what they weren’t.
Your friends and family might tell you they like your stuff to your face, but they vote with their eyeballs, and either read, respond, and share your ideas, or they don’t.
Any feedback is better than nothing
Starting out, my reach on X was tiny, just a couple of hundred followers, so the data I got was pretty minor.
But seeing if 3–5 people viewed or liked something gave me more information than I ever got out of a Google doc.
LinkedIn was a bit better, where my areas of expertise in Strategy, Product Management, and OKRs seemed to resonate with more people.
The alchemy of daily shipping
Why does it work? How does it work?
I don’t think anyone really knows, scientifically.
But it definitely does. The stats don’t lie.
The below is a screenshot of my X stats, including before, and just after my successful completion of the 4/28 writing challenge:
The easiest way to learn a daily posting habit?
Join a challenge, and post every day for 30 days.
You can see in the screenshot above that once the challenge ended, I had learned the habit, and continued posting daily, sustaining the success I had started.
All I can say is, It works.
Takeaway: If you want to start writing content that connects with your readers and helps them solve their problems in ways only you can, start posting every day. Just write and post a single small idea. Put it out there on X or LinkedIn. See what resonates. Only then should you double down and invest in writing more.
Realize that daily posting provides the momentum that will power your online writing flywheel.
#2. Never start with a blank page
This is the single biggest difference I’ve learned that separates writers who wait for inspiration, and those who can write and post consistently.
The secret is the most obvious approach: bullet out ideas of a topic you know well.
Even this piece started as a simple set of bullets.
A hierarchy of bullets
Pick a lead bullet and turn it into a headline or a hook.
- Write out your main bullets
- Then use sub-bullets…
- To develop your logic flow
Now you have the outline of your piece.
Writing with bullets has totally transformed writing for me, allowing me to sit down and start writing every day.
Takeaway: Shift from “just writing” to:
- Sourcing new idea bullets
- Bulleting out ideas that have shown promise
- Turning bullets into headlines, hooks, sentences, and paragraphs
- Edit for clarity, brevity, & readability
This will help you start to think in the organized, structured ways that underpin great writing, and you’ll start to see bullets everywhere.
#3. Be willing to invest in yourself and your writing
A big part of writing success involves continuously upgrading your skills and never stopping learning and growing as a writer.
It’s OK to start on your own, copying what other online writers are doing, applying their approaches to your writing and areas of interest.
But if you want to truly accelerate your writing, understand that you have to be willing to invest in yourself.
Who to follow?
There are many, many great thought leaders in the online digital writing space, offering challenges, courses, and ongoing communities.
I can’t tell you which ones will be the right fit for your interests and mindset.
In addition to Todd Brison, Tim Denning, Dickie Bush, and Nicolas Cole, I’ve been inspired and learned a great deal from:
Look at a number of them, and decide for yourself. But be willing to spend the money necessary.
An example of learning applied
As part of Tim and Todd’s “Mastermind,” I learned some key distinctions around writing better headlines and how to write better for Medium, one of my preferred platforms.
While my best-earning Medium articles up to that point had been up for a year and only earned about $100, learning these key distinctions allowed me to write and ship an article that earned more than that in the space of a single week!
Takeaway: If writing online is something you’re serious about, be willing to pay the money. You could certainly do it for free. But investing in yourself can truly turbocharge your writing progress.
#4. Community is the heart & soul of writing
“Faster alone, further together.”
–Attributed to an African proverb
Writing can seem like a lonely activity.
Interestingly, digital writing success means you have to work on more than just writing.
And the next most important step in getting really good and finding your audience is counterintuitively to connect with other writers.
The benefits of a writing community
Feedback is a crucial part of the process. It’s only through a community of like-minded writers that you’ll learn when your stuff is good, when it needs to be improved, and ideas on how to get better.
Sometimes I might be at a loss for new ideas, but reading someone else’s work and commenting on it helps spur a thought I can spin out into something longer.
Or even, at times, replying to someone else’s comment on my own writing can prompt the foundation of a new synthesis of two ideas.
Connect with those across all 3 phases of the writing journey
You’ll want to make an effort to connect with three different kinds of writers:
- People who are at about the same point in their journey as you are — similar length of time writing online, similar numbers of followers. They will become your collaborators, supporters, and accomplices.
- Those ahead of you on the journey — they will become your mentors.
- And those just getting started — If you remember the Feynman Technique, the best way to learn something is to teach it to others.
Takeaway: Find and connect with a like-minded community. Be open and connect with different people to find the right match in terms of temperament, interests, and writing style.
#5. Learn to access Flow States
“This is the real secret of life — to be completely engaged with what you are doing in the here and now. And instead of calling it work, realize it is play.”
– Alan Watts
I initially learned about and was able to access Flow States during my tennis, aikido, and drumming practices.
Later, I learned about the power of flow states in writing from Dr. Mehmet Yildiz, and later Tim Denning.
I can’t overstate how transformative writing in Flow States can be. The more you can access them, the better your writing will be, and the more enjoyable your writing experience will be.
Takeaway: Remove distractions. Learn about and access Flow States to achieve new levels of writing that connect with your readers.
Takeaways and TL;dr:
Due to these five small simple mindset shifts:
#1. Write and Ship Something Small Every Day
#2. Never Start with a blank page
#3. Be willing to invest in yourself and your writing
#4. Community is the heart & soul of writing
#5. Learn to access Flow States
I have gone from actively avoiding and not writing for weeks or months, to looking forward to sitting down and writing every single day.
And I’d never go back to not writing.
Daily writing and shipping, and focusing on the above five points has literally transformed my life.
Parting words: Don’t quit your day job
My advice to you?
Embrace your 9–5. Embrace creating on the side before and after work. Invest in your writing and yourself.
And one of the most unexpected benefits is the renewed focus and energy I’m able to bring to my 9–5.
– Partly because it gives me the structure to write.
– And partly because it gives my family stability.
– And partly because I learn so much in my day-to-day life that becomes part of my writing.
By writing about things you know and are good at, you might rediscover all the things that are great about your 9–5, and approach it actively.
You never know where it can lead.
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