Steal these Daily Habits of Self-Employed Entrepreneurs

Lessons from 50 Interviews with Founders, Nomads, and Authors — and How I Reached Them

Corey Breier
Nov 18, 2016 · 7 min read

In the wake of The 4 Hour Workweek’s success, the field of ‘lifestyle design’ has exploded. There are now dozens of blogs, books, and podcasts dedicated to helping you quit your job, travel the world, or live your dream. The path to self employment is well-documented, if conflicting: some say to Choose Yourself, others to Awaken the Giant Within, or perhaps the straightforward Think and Grow Rich.

Yet while the lifestyle design path is clear, there are few resources conveying what a life looks like after it is designed. What do you do all day once you’ve broken away from a regular paycheck ? How do you stay focused when there’s no boss to keep you on task? What does a happy, healthy, and productive day look like lived on your own terms?

During a recent period of unemployment, I found myself facing these questions head on. I resolved to answer them myself by directly asking people who would know — self employed entrepreneurs.

I ended up with 50 interviews from influencers like Fluent in 3 Month’s Benny Lewis, Zenhabits’ Leo Babauta, Ego is the Enemy’s Ryan Holiday, Entrepreneur on Fires John Lee Dumas, and dozens of other self-employed nomads, authors, bloggers and podcasters. The result was The Habitual Hustler, cataloguing the daily habits of 50 self-employed entrepreneurs. It’s both a map of the modern self-employment and the answer to a universal question.

Here, I’ll explain how I got these busy people to talk to me, what habits they had in common, and how my own routine has changed since starting the project. Whether you’re unemployed, self-employed, or just plain employed, we can all learn a thing or two from these habitual hustlers.

How I Got Busy People To Talk To Me

How did I manage to get in touch with these busy people? It turns out a combination of personalized cold emails, authentic interest, and friendly referrals goes a long way.

Cold emails are an art. I used the copywriting technique of AIDA — get Attention, attract Interest, arouse Desire, and inspire Action. For me, this meant starting with an authentic statement of how their work had touched me, describing my project and the benefits it would provide, and then making it as easy as possible to say yes.

Using interviewee Ryan Holiday’s tactic of ‘trading up the chain’, I started with the most accessible entrepreneurs first and used their credibility to garner introductions to the least accessible.

I made it as easy as possible for them to say yes, by adjusting the ask depending on the person. For some, it’s be a 30 minute Skype interview — for others, simply a few questions over email.

So did these hustlers have anything in common? As it turns out, there were a few commonalities I noticed amongst the interviewees. But there were also several commonly held productive beliefs that turned out to be myths.

The First Habit Commonality — Maker Morning, Manager Afternoon

The definition of self-employment is being your own boss. So one of the most important skills involved is self-management. And the vast majority of my interviewees had arrived at the same solution for this issue: maker mornings, and manager afternoons.

In other words, they would focus on creative output in the first half of the day, while deferring emails and other administrative tasks to the afternoon. This allowed them to capitalize on their creativity in the morning, when their energy is at its peak, and allocate the menial tasks for the evening, when less attention is required.

It’s hard to ignore all the other people trying to get your attention in the morning, so one must take measures to protect this sacred time. Tactics varied from keeping phones in airplane mode, restricting internet access through apps like SelfControl, or just not allowing oneself to check Facebook until 750 words had been written.

But the intention is the same — make first, manage later.

The Second Habit Commonality — Mindful Health

I had expected most of these people to wake up early in order to power through their days, but this was not quite the case. Some hustlers swore by waking early, yes — but even more reported never waking up with an alarm. As the foundation upon which they built their days, sleep, health, and exercise were paramount.

This stands in stark contrast to the productivity cult dictating harder, better, faster, stronger. But upon reflection, it makes sense. These people’s livelihood is their creative output, and your brain doesn’t work well when it’s tired. In order to maximize the quality and quantity of your output, then, you have to treat your mind and body well.

As such, mindfulness was perhaps the single biggest commonality of all the hustlers. Whether through normal meditation, gratitude journals, and just lying down for 5 minutes of reflection at lunch, almost every hustler had some kind of ritual dedicated towards presence.

This also made sense upon reflection. Effectiveness is doing the right things more than it is doing things well. Therefore, a self employed entrepreneur must slow down to confirm that they’re doing the right things.

The Third Habit Commonality — Recorded Intentions

If we have habits ensuring that one is able to do things well, and habits ensuring one knows which things should be done, it follows that the final commonality was one of recording the before and after to allow faithful self-reporting. Amongst the hustlers, this manifested itself most commonly as a habit of writing down what they wanted to do the night before.

In this way, the hustler sets an intention for the day to come, and woke up with a clear sense of direction. Coupled with a note of what had been done the day before, this habit also allows the hustler to know whether they had truly done what they set out to do.

Some recorded this in a paper journal — others with spreadsheets, and others with dedicated software. Again — the tactics varied, but the strategy was the same. Write down what you’re doing to do before you do it, and write down what you did.

Entertaining Habit Outliers

Of course, that’s not to say there weren’t exceptions to every rule. The habit outliers were just as interesting as the commonalities. Some of my favorites are listed below:

CollegeInfoGeek’s Thomas Frank schedules a tweet with a link to his PayPal account every morning at 6, so that his friends can take money from him if he didn’t wake up in time to cancel it.

Growth Hacker Janet Chang starts her days with anti meditation sessions, where she pours all her emotions out on the page to ensure rationality in the decisions to come.

Life-LongLearner’s Scott Britton has a ‘Brock Savage’ incantation before important meetings where he yells at himself in a mirror as ‘the baddest dude who ever lived’.

— Perhaps most bizarrely, Motivation Hacker Nick Winter fed $100 in small bills into a fire while repeating ‘money is not important’ in an effort to abstract value away from money.

It’s not likely many people will adopt habits like these, but at the very least, they make the read entertaining as well as instructive!

How My Routine Has Changed Since Writing This Book

The biggest changes in my routine are a recommitment to my meditation and journaling practices, a conscious attempt to defer manager work to the afternoon, and the attempt to take breaks through walks, rather than Reddit.

Small changes, with big effects. It feels good to stick to them when I know that dozens of other successful people out there are doing the same. By focusing on the process of my days rather than their output, I can trust that my daily routine will yield increasingly desirable outputs.

We’re not all self-employed yet. But we can still learn from these hustlers.

Maybe for you it’s as simple as pushing your emails to after lunch, sneaking in meditation breaks before breakfast, or just writing down what you want to do the night before. These habits are effective no matter your level of employment.

Any reader can profit from the learnings of others just like I did. By the end, you’ll know what a successful day lived on your own terms looks like — and maybe also have met a few new productivity experts along the way.

To celebrate the one year anniversary of the Habitual Hustler, grab the ebook free until November 18th for yourself or a gift for an effectively minded friend.

Startup Grind

Stories, tips, and learnings from and for startups around…

Startup Grind

Stories, tips, and learnings from and for startups around the world. Welcoming submissions re: startup education, tech trends, product, design, hiring, growth, investing, and more. Interested in submitting? Visit our submission form here:

Corey Breier

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Author on games and productivity. More at

Startup Grind

Stories, tips, and learnings from and for startups around the world. Welcoming submissions re: startup education, tech trends, product, design, hiring, growth, investing, and more. Interested in submitting? Visit our submission form here:

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