The 1 Big Mistake I Made When I Was First Getting Started As An Online Writer | RP 108

The 1 Big Mistake I Made When I Was First Getting Started As An Online Writer

I've sunk over 10,000 hours into learning how to write online.

Like most beginners, I made hundreds of mistakes since I began my online writing journey over 9 years ago.

This cost me years of growth. Here’s a snapshot:

• I chased shiny objects.

• I ignored feedback loops.

• I took on new projects, without regard for the opportunity cost.

• I added more, more, more to my life, instead of culling distractions.

• I followed “proven playbooks” from gurus like it was the Word of God.

But this mistake was the biggest one, by far:

I didn’t bias towards action

What does this mean?

• I got caught up in the planning phase of projects.

• I was afraid to “build fast and break things.”

• I would do research, consult experts, and write out an entire roadmap… Before ever taking a single step.

Here’s why I made this mistake:

I'm pretty risk-averse

I’ve spent $10,000+ on courses, coaches, and consultants trying to find the perfect playbook. Here’s a few of my investments over the years:

• $2,500 on a productivity coach

• $4,000 to learn how to write online

• $2,500 to learn how to build a coaching practice

• $750 to learn how to grow a newsletter

• $750 to learn how a creator’s YouTube business works

The list goes on. This doesn’t take into consideration my subscriptions to online course libraries like Masterclass, Wondrium, Skillshare, and CreativeLive.

I was trying to see the roadmap all the way until the end, before I even took a single step.

The end result? It took me a long time to take the first step of publishing online.

I hated dealing with the unknown

I waited until l had the ideal circumstances and had the recommended tech stack to get started.

• For weeks, I copied the newsletter formats of half a dozen writers and creators because I didn’t trust myself to figure it out.

• It took me months to build out a second brain (yes, I took Tiago Forte’s Building a Second Brain) because I wanted to be prepared for any and all potential scenarios.

• It took me years (and 10 notebooks) to get my bullet journaling practice to where I wanted it to be because I was so afraid of messing up.

I took “future-proofing” to the extreme… And it led to even more procrastination.

I lost my way amidst all the fancy tools

Here’s a short list of the tools I’ve tested for my notetaking system, writing workflow, and media business over the years:

• Evernote

• Roam

• Obsidian, including Obsidian Publish

• Notion

• Fantastical

• Google Calendar, Tasks, Keep, Docs, etc.

• Bullet journaling (not a software)

• Convertkit

• Aweber

• Mailchimp

• Beehiiv

• Substack

• Squarespace

• Webflow

• Hypefury

• Typefully

• Ulysses

Of course, none of these tools are bad. (In fact, I’ve included my current writing tech stack here, alongisde the software I no longer use.) My point is this: most of the time, the potential benefit of a shiny new object isn’t worth…

• The cognitive cost of a distraction

• The interruption of systems and loss of momentum

• The switching cost in terms of time and cognitive load

So should you use Convertkit, Substack, or Beehive? If you’re just starting out, that’s not the right question to ask.

Just pick one to start. And keep going.

I forgot why I got into this in the first place

Instead of thinking about how I could publish remarkable writing and create quality content, I consumed the content of one expert after another.

Instead of increasing how much I published, I subscribed to clever strategies that promised outsized results... Only for my numbers to inch along like an unwilling toddler.

The problem with following someone else's success playbook (to paraphrase Andrew Chen’s the Law of Shitty Clickthroughs) is that the strategy's effectiveness will have worn off by the time the creator…

1. Discovered the strategy,

2. Milked it, and

3. Packaged it into a course.

My point here isn’t to invalidate the courses I took or the software that I tested.

Biasing towards consumption versus action set me back for years. Waste of time or not, I needed every single one of these side quests to teach me to the other side – to bias towards action. It's worth acknowledging it still taught me a ton.

Today instead of endless consuming, I do just enough research to figure out the minimum viable action I can take. So I can get to the execution stage as quickly as I can.

Metalearning: What it means to “bias towards action”

Biasing towards action is a much more effective rule of thumb to figure out what works for you. It…

• Increases iteration velocity, generating more data points to analyze and more reps to compound improvement.

• Allows you to analyze data points as they come, instead of losing your mind trying to predict what could happen.

• Lets you write your own playbook for our current situation… And for future ones.

Here’s my metalearning method to write my own playbooks:

1. Learn the minimum viable action I can take to generate data points

2. Get as many reps as I can sustainably do in a 4-week period

3. Analyze the data. Pinpoint what works, what to do more of, and what to stop doing.

4. Increase iteration velocity when possible.

5. Rinse and repeat.

Thanks to this simple action-reflection feedback loop, I feel so much more comfortable learning other people's strategies and making them my own.

And I hope learning from my mistake helps you, too.

😉 You're welcome

A selection of interesting links & fun recommendations.

• 📚 The Little Prince by Antoine de Saint-Exupéry. This book reminded me about the joys of useful work and simple leisure and the ridiculousness of adulthood. Most importantly this books reminded me to chill; most of what I consider matters of consequence, have none.

• 🐦 A simple checklist to see if your company is taking care of you… Or setting you up for burn out. 

• ❝ Quotes I’m pondering: