What writing 300 newsletters taught me about life and business

300 weeks ago I sat down and sent an email to 36 friends. I wrote the email in Gmail and signed of with the following:

“Not sure when I’ll have time for the next one.”

Welp. 2 kids later and with less hair on my crown, look at where we’ve landed.

Some back of the envelope math (based off of a 44 hour work-week) shows that I’ve cleared the Gladwellian threshold of 10,000 hours by 30%.

It’s been an incredible ride and tbh a bit disorienting. In some ways, the 6 years flew by. Today, RadReads definitely feels more like “a job.” Yet it also feels like things are just getting started.

I guess two things can be true at once.

To honor this small milestone, I fielded a mega-thread of questions from RadReaders across the globe. The questions run the gamut across habits, process, motivation, monetization, and regrets. Some will resonate more than others, but make sure you read the very last one.

(I was also challenged to use memes, which is something my 40 year old brain can’t process – but I gave it an honest effort.)

How do you keep yourself accountable to write consistently?

This was by far the most frequently asked question (and is probably why Atomic Habits has sold > 4 million copies). Writing each week definitely falls into the four-part model below:

The 3 R's of Habit Change: How To Start New Habits That Actually Stick
  • Cue: “Oh crap, it’s Saturday morning.”
  • Craving: “Here’s an opportunity to express myself creatively and connect with friends”
  • Response: A solid workflow (detailed later) that ensures the newsletter can be written in less than 3 hours
  • Reward: The wonderful interactions with readers who regularly hit reply to the RadReads email

But I’d be lying if I said that this alone could sustain a solo (ish) effort over the past six years. One of my unofficial mantras as an entrepreneur has been: Follow the fun.

I’ve pursued projects that have been fun. And abandoned those that felt tedious. (Stated differently, I fundamentally believe that you can create rad things without unnecessary struggle.) As an entrepreneur, this has definitely felt indulgent at times (and prompted some hard decisions), but it’s why 6 years later I’m energetically still in the game.

What’s your process and checklist?

I know you’re expecting some fancy automated process with many bells and whistles. I’m sorry to disappoint. The process very basic (or as kids these days say, cheugey).

I read articles across Twitter and 50+ email newsletters. When an article grabs my attention, I add it to my library using the Notion clipper. This creates a new instance of the newsletter:

And then my colleagues help me write the blurbs and insert them into our email provider, ConvertKit.

At what point did you move from “this isn’t gaining traction” to “this is finally gaining traction?”

For me, traction was simple. Can this activity (i.e. RadReads) support our family’s lifestyle? Now you may be tempted to believe that being anointed Oprah for Millennials or the Wall Street Guru would be the inflection point for the newsletter.

It turns out that traction came well before the “press hits” (and the ensuing spikes in readership). Traction came in the form of inbound emails from early readers responding to the RadReads email asking, “Will you coach me?” And while I hadn’t set out to become a coach, I realized that not only was there demand for coaching – but I really enjoyed it. (The second moment of “traction” came in 2018, when I launched the first cohort of Supercharge Your Productivity.)

How do you think your life would have been different if you didn’t branch off from the original plan and start this newsletter (and your new way of life)?

I never set out to be an Internet entrepreneur. I honestly didn’t think I had it in me to be an entrepreneur. When I left Blackrock in 2015, I thought I’d take some time off and then join an early stage start up. RadReads was just a creative hobby that would keep me busy during this transition period.

But then a funny thing happened.

By following the fun, so many new pathways introduced themselves. It turned out that I liked writing. People cared about what I had to say. Some, were moved by it. Before I knew it, I had a business to manage with contractors, taxes, financials, customers and marketing.

And as we’ll explore below, that’s mostly a good thing (that also comes with some unintended consequences).

What’s the largest failure you faced and what lesson did it teach you? Do you regret anything?

At the risk of sounding arrogant, I don’t think I’ve had any failures. But I have spun my wheels and wasted a lot of time on things that didn’t matter. These include:

Writing a book proposal

After the Oprah for Millennials article came out, I was approached by a bunch of agents and book publishers. My ego felt great. I said to myself, “This. Is my moment.” And went down the path to write a book. The truth was, I wasn’t ready.

I didn’t have a Big Idea.

I didn’t have enough of an audience.

I wasn’t a particularly talented writer.

When I submitted the proposal, it was met by a chorus of crickets. The process occupied a good 4 months of my life, and I left with very little to show for.

Chasing the next sexy medium

As an Internet entrepreneur, there’s a bottomless pit of FOMO around new channels, platforms and methods of distribution. You see someone crushing it on Instagram, nailing the YouTube algo, or amassing hundreds of thousands of followers on Twitter and say to yourself “I should be doing that.”

In the early days, I’d easily fall into these time traps, thinking that this Shiny New Toy would make everything click. But that never happened, and in fact, doubling down on what I was naturally good at (email and blogging) was – in hindsight – always the best course of action.

I often get asked the regret question. Not just about the past 6 years, but about my life more broadly. I don’t have any regrets. Which doesn’t mean I haven’t made my share of mistakes and bad decisions. Instead means that I am the amalgamation of my lived experiences – both good and bad.

How are you reinventing your approach so that it feels enjoyable for you to continue creating?

This was by far the hardest-hitting question that I received. The truth is that when you do anything for 13,000 hours, the repetition alone will dull the spark. And for years, I patiently yearned for the day that RadReads would be profitable (Year 5). Yet once that happened, a funny thing kicked in: the when-then trap. And I yearned for the days where I could let my creativity roam free.

TBH, it’s the question I wrestle with on a daily basis. I know the spark is there when I write posts that are more adventurous and less “service-y” (i.e. How to [fill in the blank]). I know that the spark is there when I’m teaching. It’s there as I grow the team and watch others thrive. Stay tuned on this front.

What does it feel like to bet on yourself and win?

I honestly did a double take when I read this question. My first reaction, was “Win, I barely break even on my living expenses?!?!”

(My second reaction, “But James Clear has a 1 million person email list.”)

But then it hit me. Sure, entrepreneurship is a game. And 6 years later, it feels a lot easier. But it’s not THE game.

The real game is how I show up for my family. It’s the inner voice I use to talk to myself that no one will ever hear. It’s navigating the health flare ups that come with being in your 40s. And in that game, I’m still growing, still getting to know myself better, and still learning to love with more intimacy – and a more open heart.

That’s the game.

And with that, I thank you. Thank you for your support over these past 6 years. The words of encouragement. Replying to my tweets. Taking a flyer on my courses. Thank you for being so rad.

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