How and Why I Wrote a Book About Entrepreneurial Habits

One year ago, I embarked on a journey to interview 50 self employed entrepreneurs about their daily habits. Now, the result of all those hours of research, outreach, and interviews hits the Amazon store. Here’s why and how I did it.


A Google search for Lifestyle design exposes hundreds of people making livings off the internet and doing whatever they want on a regular basis. You’ll also notice that these people readily share tips, hacks, and resources for you to do the same. The internet is awash in methods that promise to get you self employed.

However, there’s not much content on what your life looks like when you’re self employed. How does one stay healthy, happy, and productive when you can do whatever you want?

This was the question I found myself asking last September, when I lost my job and my girlfriend in the same week. Suddenly I had a lot of time on my hands, and I didn’t know how to apply it constructively. I knew I wasn’t the first person to face that problem, given my enduring passion for online entrepreneurs, but I realized I didn’t know what any of their daily routines looked like. Couple that with a reading of Mason Currey’s wonderful Daily Rituals: How Artists Work, and I had a draft on my hands.

Interviewing self employed entrepreneurs would accomplish 3 things:

  • Answer my original question for me and the world (this content didn’t exist)
  • Provide a pre baked marketing solution (promote to their followings!)
  • Allow me to personally connect with dozens of my personal heroes.

Nobody wants to spend 25 minutes of their life talking to an internet stranger, but if it’s for a project that may increase their stature or following, it’s surprising how accessible people are.

Indeed, you can see this in the proliferation of modern podcasts where people talk to their friends and broadcast the result along with a sponsored message. I didn’t want to go the podcast route for a few reasons:

  • I’m a reader by nature — I take in information better through writing than listening. The best podcasts were the ones I had to listen to again to take down notes, so why add that extra step?
  • I noticed anecdotally (and from interviews) that the only people who listen to podcasts are those with commutes or workouts, and I saw no need to pigeonhole myself as such.

Worst case, readers would skim my book, but at least they would pay attention to it. With a podcast, your audience is far more narrow, commoditized, and requires a higher degree of commitment. Ergo, a book!


With the interview format, my task was not writing an actual novel but getting the attention of many internet famous individuals. This is an invaluable skill — I first learned it during my job hunt last year, and now as a marketer at a startup, you can boil my job down to 3 things: convincing investors, partners, and press to give me attention. Therefore the process of writing the book was intrinsically valuable, not to mention fun — I got to talk to my heroes, and find more!

The beginning was easy — I started with the least famous entrepreneurs, who were a simple friendly cold email away from saying yes. Much of their audience is found through podcast interviews, guest posts and the like, so I was just another half hour Skype interview in their schedule.

I asked them what their daily routine was, how they shaped their workspace and mental processes, tools and information they’d recommend, as well as the single habit they’d most recommend to an aspiring hustler. I also asked them whose habits they’d like to see next, which allowed me to have each interviewee refer me to the next with a warm introduction.

Once I got farther up the pecking order, things got tougher. Many interviewees were authors and creatives who knew they needed to shut out intrusions from strangers like me in order to get work done, and there was nothing I could say to get around that. However, for the top of the chain, I found that many of the answers to my questions were already online, just scattered throughout several locations. So with them, I gathered as much public info about their days as I could, and then used warm introductions or blatant tweets to get their permission to be included. Nobody said no to that!

The trickiest ones were the famous people who didn’t have info online. I ended up asking them to record themselves talking through my questions and sending the resulting voice memo to me to transcribe, which took around 7 minutes and didn’t require scheduling, unlike 25 minute Skype interviews. This worked, but resulting in less detailed profiles.


In retrospect, I could have made this book much more easily, by focusing solely on quick interviews or recorded voice memos, having FancyHands assistants transcribe them, and having Upwork assistants edit and format the thing into a book. With a format like this, there’s no reason to give yourself more work than necessary. But it was a labor of love, so I don’t regret it.

However, I did notice my interest in the project lagging towards the end. By the time I had completed all interviews, I had kind of answered my original question, and all that remained was grunt work and book marketing. I had written the book I wanted to read, and now that I read it, I didn’t care enough to go big on marketing, which is a problem because book marketing is just as big of an undertaking as the book itself.

I decided to use Amazon for the increased visibility and distribution, rather than hosting it on my own site, where few if any people would find it after the launch. I decided to make the book free for the first two days, to make sharing and downloading easier, and to shoot it up the charts. It’s a common practice I learned from two of the interviewees: Taylor Pearson and Scott Britton. We’ll see how it works out.

As for the marketing, interviewees Ryan Holiday and Charlie Hoehn have fantastic guides on that. However, I measure success like Ryan:

“Authors should measure success by the assets they’ve accumulated via the platform they’ve built. This means emails collected, partnerships made with influencers in your space, speaking gigs, evergreen content placements on blogs”.

I’ve already got partnerships with influencers and evergreen content ready, so all that’s left to do it put it to work. Sales and profit are less important than connections, and with smart promotion, those will come in spades.

What next?

So, what next? I know what a well-structured day looks like, and I’ve mapped the self employed creative space to my satisfaction. However, interviewing smart people to spread their knowledge and create connections is a winning formula — I could see highlighting self employed entrepreneurs who fit into timely themes, like snake people or the sharing economy, or startup founders with actionable tactics. We’ll see.

Anyways, go read my book! You’ll learn about tons of successful habits, discover new self employed entrepreneurs, and be awash in resources to continue the journey.

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