Learning on the job, rejecting work life balance, and buying one-way plane tickets to Brazil with Michael Kapps (Working Jobs Radio Episode 2)

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Michael Kapps is our generation’s international man of mystery. An adventurer above all else, our friend followed his gut across all different types of continents starting companies, making art, and sometimes working as a ranch hand. I met Kapps while we were working together at McKinsey & Co and knew right away that he was up to something big so it didn’t come as any surprise when I heard he’d moved to Brazil to start a company. Less than two years later, his company, Tá na Hora has served thousands of patients, building the technology to bridge communication between patients and physicians.

In this episode, we talk about his decision to buy a one-way ticket to Brazil, rethink the concept of work-life balance, and explain how sometimes you can’t learn things until you do them.

To learn more about Kapps and Ta na Hora, go to medico.com.vc 


  • How poorly education or traditional jobs prepare you for entrepreneurship
  • The irreplaceable value of trying a bunch of things to see what sticks
  • Why competition is for suckers and how a challenging geography can be an advantage
  • Why making your work your life can be better than trying to balance work and life
  • How to learn through experience

If you enjoyed this episode, subscribe to Working Jobs Radio on iTunes and consider leaving me a short review--it really helps for new podcasts. 

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Our immigrant parents want us to write poetry (they just might not know it yet)

Adapted from Working Jobs. I'll be sending out advance review copies within the next month, so if you'd like to read the book before it's out, sign up for my weekly newsletter

When I was young, I’d spend every third or fourth summer in Shenyang, China, visiting my family. Upon arrival, my mother, father, and brother would gather with two sets of grandparents, uncles, aunts and cousins for a feast. And for the duration of the trip, those same loving faces were always available to travel, eat, and play with us. Several weeks later, our bags packed for our return to the U.S., we’d gather again for a final meal, our faces radiating red with joy, tears, and asian glow (as it turns out many Asians are allergic to alcohol and flush bright red with so much as a drop).

I spent my first few trips in blissful ignorance of my Chinese family’s lives outside of our infrequent visits. As far as I could tell, they lived a happy and celebratory life, filled with food, friends, and family. But as I grew older and more proficient in Mandarin, I started to develop a more complete perspective on my family members.

Most of what I learned isn’t special to my family–just a child’s increasing awareness that other people have good days and bad days, challenges and blessings–but one story blew my mind and sticks with me to this day.

My parents grew up during China’s Cultural Revolution, so my grandparents were working adults in a period of intense persecution and violence. Mao Zedong and his party sought to eradicate any capitalist remnants and reinforce communist ideologies across the country. Those associated with capitalist tendencies suffered public humiliation, arbitrary imprisonment, seizure of property and, in the case of my grandfather (on my father’s side), forcible displacement to rural regions.

My grandfather was sent to a farm hundreds of miles away from his family to learn from the peasants and farmers. For years, he spent his time on the farm and would, when permitted, travel for days to visit my father, aunt, and grandmother. This prolonged injustice not only took away years of his life that he could have spent with family and friends, it also impacted his work. At retirement, he would receive a dramatically smaller retirement check because of the shorter length of his career. His previous employment: rocket scientist.

This story surprised me. Growing up, my brother and I thought that all of our family members were superheroes and impervious to any unfavorable conditions. I have one memory of my grandfather visiting us in America. We were waiting at an intersection in Chicago and he pulled out a stack of hundred dollar bills. I’d never seen so much money in my life, so I asked him if he was the Richest Man in the World. He “confirmed” our suspicions, and my father reminded us that he was, after all, a rocket scientist.

It never would have occurred to me that my grandfather was part of what historians consider China’s “lost generation.”

Our family’s tales described each of its members as infallible and successful by adhering to a consistent set of values. My grandfather was the Richest Man in the World because he was smart and hard working. Sacrifice was a primary characteristic ascribed to his success and was often invoked when my brother and I wished to play video games or hang out with friends instead of read or practice. They were storylines designed to prepare us for the future; a future that they knew was full of sacrifice. Through these stories they tried to set our expectations so that we might enjoy an adulthood happier than their own.

Implicit in the construction of their stories was the assumption that our life’s conditions would resemble their own. In their world, one’s working life did not change meaningfully across its duration, and the nature of one’s work was determined by the nature of and level of one’s education. Given that one’s work was a primary form of pride (remember my grandfather was a proud rocket scientist,something my family and our neighbors and friends in China loudly revered in spite of an their own objectively unfavorable economic outcome), competing viciously for the few spots at a top school consumed the attention of students and their families because you had one chance to gain entry into a life of prestigious work, a life that became a reliable part of your identity.

It was also a world where no matter how much you worked, work was still work. One did not expect to become boss and would never dream to become their own boss (of course that has changed today as China has grown more capitalist). Work was a stepping stone to give your next generation better opportunities. Work was a sacrifice to provide for your family. And work was good, honest-to-God paying your dues for the community.

I’m 25 years old as I write this, and the world in which they  they lived and worked and romanticized in stories is not a  world that exists any longer. I am part of  a generation that is overeducated and underemployed, disenchanted with the idea of a consistent career, with eyes far, far bigger than our stomachs.

The conditions have changed, but their stories still impact us. So, when we’re upset with the path previous generations have enabled for us, we experience guilt. Someone further back in our lineage sacrificed and sacrificed to give us the opportunity we have today. Are we really just going to turn up our noses up and search for some elusive, meaningful job that we can’t even describe?

When I asked my friend Dayo Adesokan, a Biomedical Engineering student turned comedy writer, about this, he said:

We’re both children of immigrants, so on some level, sure not everyone in every country at any given time will be able to pursue their passion, but what my grandparents and parents did gave me the opportunity to do so. It could be that at some point in time, future generations of any given family can pursue what they’re passionate about.
I think maybe the older generation measures happiness differently from our own. My dad’s goals in life were to get educated, to get a good job, to have a wife, and to raise a family. He told me he became an accountant because, at the time, accountants made more money than doctors. Otherwise, he would have become a doctor.
Now, that’s not how I’d have gone about choosing a career, but that’s how he measured his happiness.

How can we rationalize the sacrifice of previous generations with our individual pursuit for meaning here and now? These decisions fly in the face of the values of our forefathers.

My senior year of high school, I took a course called Modern Poetry. At the time, Donald Hall sat as the Poet Laureate, so we read some of his books. I only remembered one line from the entire course and it is this:

grandparents toil in the fields to give parents opportunity to go to school, parents toil in the office to give kids chance to work on what they want, kids go and become poets… LifeWork

Every generation in the past has worked to make it easier for the next. Previous generations have made it possible for me to even think about the concept of finding fulfillment in work. Their sacrifices opened up the space for me to begin exploring these problems, and the very process of thinking about these problems makes me feel this complicated sense of guilt. I perceive my environment as disapproving of my generation’s desire to “become poets,” but it’s this very opportunity to love what we do that previous generations had worked so hard to achieve.

Download the first 25 pages of Working Jobs for free. Click here. 

Learning to fish, the 10,000 Rule, and the Power of habits with Dayo Adesokan (Working Jobs Radio Episode 1)

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Dayo is an old friend from high school, who, like me, originally planned to pursue medical school only to drop it at some point during college (also like me!). After finishing his degree in Biomedical Engineering, Dayo went on to get an MBA, worked in finance briefly, and then realized he wanted to be a screenwriter. He moved to NYC, performed standup, and started writing comedy. About a year ago, he got into the CBS Writer’s Mentoring program, and moved to LA. 

You should read his spec scripts at dayolawson.com and follow him on twitter @perdiemperdayo.


  • How meditation helps manage the ups and downs of the creative process
  • The allegory of the fisherman and the businessman
  • Discovering comedy as a calling
  • Why writing was “it” but performing stand-up was not
  • What makes him believe he can make a career doing what he loves
  • The importance of finding peers that can give you feedback on your work
  • How to balance a “day job” with a personal passion job
  • Letting go of future outcomes and focusing on the process
  • Why he has a tattoo of the number 10,000


  • Headspace 
  • Hannibal Buress
  • Einstein
  • Demetri Martin
  • Charles DuHigg’s The Power of Habit gr
  • Malcolm Gladwell’s Outliers gr
  • Jonathan Saffron Foer’s Eating Animals gr
  • Robert Greene's Mastery gr

If you enjoyed this episode, subscribe to Working Jobs Radio on iTunes and consider leaving me a short review--it really helps for new podcasts. 

Subscribe to my weekly newsletter for the best stuff from the blog, the book, and the podcast. Click here

Introducing Working Jobs Radio: a podcast about people who love their jobs

Request: please go to my page on ProductHunt and upvote the podcast. If you need an invite, email me and I'll invite you (I have six invites). 

When I first started the Working Jobs project, I wanted to answer one question: “how do we do what we enjoy for a living?”

Before I’d considered the book or the podcast, I’d been asking myself that question over and over again in my personal journal. I’m not sure I ever explicitly stated the question, but I was constantly writing things like:

  • Why do people dislike what they do?
  • What keeps people in jobs they hate?
  • How can you tell what your passion is?
  • Does everybody have a passion or calling?
  • Is disliking your job necessary for financial success?
  • What’s the relationship between job success and happiness?
  • How did we get here?
  • How do we get out of here?
  • What does the future of work look like? Are we happy in it?
  • Are we prepared for it?
  • How do I make a living doing something I enjoy?
  • What do people that love their work have in common?
  • What happens when more people enjoy what they do?
  • What happens if all of us enjoy what we do?
  • What would need to happen to make that possible?

These questions covered my consciousness like a fog and demanded that I answer them before I proceed any further.

I read 52 books in 2014. Not all of them were read in service of these questions, but many of them where. I wrote more than I’ve ever written in my life. I quit my job to write a book.

It was a solitary practice. Each day I’d wake up and slowly disperse more of the fog. I felt alienated. I was unsure of myself and could sense disbelief from all corners of my ring (bosses, family, colleagues, friends).

Then, something cool happened.

I started colliding with other people who had made similar leaps. Slowly, at first: I’d reach out to my friends who were already successful musicians, actors, entrepreneurs, etc. and ask them how the hell they survived the early days. Then, more and more quickly. As I shared more of my work with the world, the world sent me like minded people who were experiencing the same things that I was.

These conversations blew my mind. Their stories helped me find inspiration, validation and community. I realized that there was no playbook, no secret thread that ran through each of their stories, just a common experience of following intuition and finding a way to make it work.

These were the stories I desperately needed to hear a year ago.

I knew that I needed to share them. Just as I impulsively decided to write a book, I decided to host a podcast about people who love what they do: who they are, what they do, and how they got there. Their stories helped me and I thought they could help others.

There are two parts to doing what you enjoy for a living and I hope Working Jobs Radio will contribute to both.

The first is knowing what you love. This is actually very very challenging in modern society. I believe the best way to find figure out what you love is to dabble a ton. Try a lot of things. I hope the podcast will help listeners dabble vicariously through the lives of others.

The second is doing what you love. There are lots and lots of books and blogs out there that try to explain how to do this. Some are good and some are trash. Resources are great, but the best way to figure out how to do it for yourself is to get started and figure it out. I hope the stories shared on the podcast will give listeners the confidence to do that.

I’m so thrilled to share this project with the world. It has been one of the most gratifying experiences of my life and I hope you enjoy listening to it as much as I enjoy making it.

Check out episode zero (an intro) on iTunes by clicking here. New episodes every Sunday.

How one semester of college inspires top students to ditch their dreams

Adapted from Working Jobs, available March 15, 2015. If you make it all the way to the bottom there’s a link to download the first 25 pages :)

It’s no surprise that the reality of work doesn’t quite live up to the hype.

We prepare for work for so long, sitting in classroom after classroom, that it’s only well into our adulthood that we start to actually do it. In the United States, we’re expected to finish at least a dozen years of schooling, a number that has steadily increased since the Industrial Age. Spending this much time in preparation for work gives a lot of time for people, organizations, and media to influence our expectations of what work will be like. They all tell students to do their work because it will prepare them for a great career and happy life.

We accept the premise that by diligently doing what we’re told, we’ll benefit from a rewarding career and an abundant life.

This is one of modern life’s great paradoxes. We expect a lot from work, but we delay our gratification and place blind faith in the system. As a society, we write checks that instruct individuals to cash in once they pay their dues. But we’re starting to realize that these checks aren’t good anymore. This is the profound let down of our generation.

Imagine it like an investment. We don’t know it at the time, but as children and young adults we invest our ability to make decisions with our intuition for the promise of these brilliant future returns. Because our intuition is no longer “liquid”, we can only make decisions by doing what we’re told. Even if the future returns never arrive, we’ve lost what intuition we had and now have to build it back up again from scratch.

This loss of intuition enables a phenomenon on college campuses that I call the great game of musical chairs.

The game is played in the fall semester of senior year. In this game, it doesn’t matter how much you’ve actualized yourself for the preceding three years. Nobody cares how much you really, sincerely, understand James Joyce now. Tuck away your balanced but critical assessment of impressionist art until you start dating again in your thirties. Nobody cares.

For the next few months, you’re sprinting around the circle looking for an open chair. What’s more, you don’t want just any chair, you want a comfortable, ergonomic chair. You want a comfortable, ergonomic chair that’s a design classic. Basically, everybody is looking for an Aeron chair.

You didn’t care about Aeron chairs in the past, but all of sudden, everybody around you really seems to want one. So, you show up to info sessions and start interviewing for jobs you didn’t know existed until three weeks ago when you went to that Bain info session because there was free pizza. Nothing they’re saying makes very much sense but they’re dressed nicely and assure you they’ll get into Harvard Business School afterwards so now you want that job.

By the way, what I just described was just my own (and many of my classmates’) real experience succumbing to the allure of what might be loosely called the “business school track.” Equally alluring is the “law school track,” “medical school track,” and countless other tracks that seem to have a clear pecking order and cultural traditions. This isn’t to say that people who are perfect fits for these tracks, followed them, and have found purpose in their work do not exist. But more than likely they haven’t gotten this far anyway.

As my friend Tim Wu (now better known as his progressive house producer alter-ego Elephante) put it:

There’s this strong herd mentality toward these great-paying finance and consulting jobs that you see all of your friends getting. I never would have dreamed about going into either of those jobs prior to college. But once you’re there, you’re in the middle of this school of fish all swimming in one direction. So you start to think maybe there’s something wrong with me for not wanting this as well. My roommates were getting $100K starting salaries at these prestigious firms and it became this very big status thing, where people would look up to the kids who got offers at Goldman Sachs or a hedge fund. It was total group-think. Freshman year I’d have said there’s no way, but over time it just chipped away at me.

He ended up graduating Harvard to a job in management consulting and wrestled to unlearn this group think so he could pursue what he’d always known to be his calling: a career in music.

At the time, that decision seems like the least risky thing one can do. But implicit in the decision to pursue it is the acknowledgement that you can’t do what you originally wanted to do for money--that these guys in the suits will have a better idea of how to live a rich and meaningful life than you would if left to your own devices.

The irony is that if you listen carefully, it should be clear that they don’t have a better idea. How could they?

I was lucky enough to find a “desirable chair” (during that tumultuous autumn of my senior year) at a management consulting firm called McKinsey & Company, where I learned a lot from some very smart people. But I really wish I’d had the perspective to see things more clearly when I was applying.

I graduated from a math and science academy (where I relished in my English and History classes) to study Neuroscience at a liberal arts college. In retrospect, I think I was preparing myself for medical school. I spent my summers doing clinical research and nonprofit consulting and ended up forgoing graduate school entirely to pursue a career in finance, or something. I remember one interviewer laughing at me when I walked him through my resume. "I'm a neuroscience and english double major and I want to be a management consultant," I'd said, in my convincing voice I'd practiced many times alone in my room.

McKinsey took us to dinner the night before our final round interviews. The recruiters sat us in between current consultants so we could inquire about their lives and get a feel for the type of people we might be working with.

Some questions that were asked:

Q: What's your favorite thing about the firm? A: The people.

Okay cool, I get that. I went to college for the people I’d meet and am terrified that work won't provide the people inspiration that I treasured in college.

Q: How did you end up here? A: Funny story, actually, I was originally planning to do “my passion” but saw McKinsey on campus and one thing led to another and here I am.

Um... okay that's cool too. Sounds kind of like me. (Maybe these people are like me, I thought to myself, hopefully.)

Q: Why have you stayed for as long as you have? A: Well, I never planned to stay this long. I promised myself that I'd go off and do “my passion” after two years but I just kept following what felt right and here I am seven years later. You see a lot of people at the firm that stay on like that. I never thought it'd be me though (followed by a nervous laugh).

I wasn’t sure what to make of that final sentiment. It's technically a success story because this woman "made partner," but I felt a twinge of sadness in her voice. At the time, her response didn't seem so important, but I kept hearing the same story over and over again.

But maybe that was okay, because I didn't even know my own passion yet, so I looked for my first role out of college to either open doors once I identified my passion or eventually evolve to become my passion. Later that week, I received an offer.

That's the rationale a lot of young professionals use when deciding on their first job. I'll work here for a while, learn some skills, meet some people, gain perspective and then decide once I know where I want to direct my career which of these opened doors I should walk through.

Noting this, I looked around the firm to see how other consultants approached finding their careers. Though some found great satisfaction in their work and some found other opportunities through work, many (roughly half) remained at the firm in spite of themselves. They had always planned to find something more closely aligned to their passions but never did.

I learned that there’s a saying that the top 25% of consultants leave the firm for greener pastures, the bottom 25% of consultants aren’t invited to stay, and everybody leftover doesn’t have anything better to do.

It reminded me of Josh Waitzkin's meditation on incremental growth in The Art of Learning. In it, he says, "The key to pursuing excellence is to embrace an organic, long-term learning process, and not to live in a shell of static, safe mediocrity." Waitzkin invokes the hermit crab as way to illustrate this point.

As the hermit crab gets bigger, it must find a more spacious shell. So this slow, clumsy creature embarks on a quest for a new home. If it does not find an adequate shell quickly, a "terribly delicate moment of truth arises." The typically well-protected hermit crab is, for a precarious moment in time, exposing its vulnerable mushiness to predators. Though scary and potentially dangerous, it is these moments in between shells that determine our growth. Someone that does not make a mindful decision to stay with a career allows inaction to guide their growth, and in that way, resembles an anorexic hermit crab, "starving itself so it doesn't have to grow to find a new shell."

We know decisions are important. We make decisions every day about how we spend our time or who we spend our time with. But for some reason, we tend to prioritize important decisions about careers less thoughtfully than we might plan our free time. Why don’t we recognize that decisions about our careers have the greatest impact on how we spend our time on any given day, 40-plus hours per week, and even the people we spend our time with? Why are we so afraid of the space in between our shells?

If we’re not having impact and experiencing joy in the process of work, then we must be working to attain it later on. But that just doesn’t seem to be happening. “Later on,” I’m starting to believe, is now or never.

Imagine what we can accomplish if we help each other rebuild our intuition. One has to believe that we’d all work on things that mattered more, things that would bring us more joy, and things that will ultimately have a bigger positive impact on the world.

These are the “working jobs” that I’m dreaming about. That’s why I’m writing a book. If any of this resonated with you, you can download the first 25 pages of the book for free. Click here. 

Try this framework to get more done every day

I didn’t have enough time.

I’d offer myself this excuse every time I fell short of a goal or let a side-project die from neglect. It killed me a little every time that happened, but what choice did I have? I needed an excuse and this one beat I’m not capable.

When you keep hearing that you don’t have enough time, you start to believe it. I could barely get anything done at work so how could I possibly learn a new language or pick up a new skill? I wanted to start a company but if I couldn’t manage my own time how could I let others trust me with theirs?

Before I quit my job, I had to see whether I didn’t have enough time or whether I was just using it wrong. For the twenty five years leading up to this moment, I focused on changing myself. When things didn’t work out, I directed my disappointment at the core of my being. Something about me just wasn’t equipped to make consistent progress on things that I cared about. 

This time I tried to change my environment and my approach. The result is this routine. It’s still a work in progress but it has kept me from going crazy and losing all hope so far.

By the way, this is a framework I use to manage my time since quitting my job. If you want a weekly digest of everything I'm learning from working for myself, sign up for my newsletter.   

The order system

Everything I do is either a first, second, or third-order task. Each task is assigned an order based on its urgency (y-axis) and creative difficulty (x-axis). In this framework, creative difficulty literally means how much energy is required to create something that did not exist before. 

First order work

Tasks that require creative energy or focus. The quality of these tasks matter. These are the tasks that need to be redone if you don't get it right. I spend this time writing, designing, or strategizing.

First order work demands no distractions and clear thinking. For me, this happens in a two hour block right after I wake up. I make coffee, meditate, and start my first-order tasks. I don’t check my phone or my email. I clear my mind and start working.

Second order work

Tasks that are critical to the success of whatever you’re working on. I spend this time editing, communicating, debugging, and coding.

Second order work comes after the completion of first order work and a break to recharge the brain. I take a break after completing first-order work to shower and go to the gym. Then, I sit back down and work until lunch.

Third order work

Tasks that are mundane and less urgent, but still important. I spend this time doing repetitive tasks that should eventually get automated like doing data entry.

Third order work can come whenever you have time and feel like it, because task switching and distractions are less costly for these more mundane tasks. I do these throughout the day when I’m bored or my brain feels fried.


“Working smarter is better than working harder” just means do the most important thing at any given time. If you take away only one thing from this framework, it’s to do the tasks that require the best of you before you do anything else. The other stuff just falls into place.

A typical day of mine looks like this. This works best for me because I love the mornings, but you could move things around to suit your needs (like if you were a night owl):

  • 6:00 - Wake-up 
  • 6-6:15 - Coffee 
  • 6:15-6:30 - Meditate 
  • 6:30 - 8:30 - First order tasks 
  • 8:30 - 9:30 - Break
  • 9:30 - 11:30 - Second order tasks 
  • 11:30 - 12:30 - Lunch 
  • 12:30 - 6:00 - Periodically do Third order tasks while I hang out with my girlfriend, read books, etc. 
  • 6:00 - 7:00 - Dinner 
  • 7:00 - 9:00 - Hang out with people and read
  • 9:00 - Bed

Sometimes I don't feel like doing third order tasks and just call it a day after four hours of deliberate work. Before, I let my anxiety about productivity poison my free time. Now, I can actually enjoy my free time knowing that I've made progress on my most important tasks every day. It's bizarre. I get more done but spend fewer hours working. 

It took me a lot of trial and error to come up with a routine that balances getting stuff done and making sure I don't burn out. This works for me but might not work for everybody.

What works for you? 

Recommended reading: Your Brain at Work gr

My current first and second order tasks all focus on writing and publishing a book about our generation's relationship with jobs. I'm sharing the whole process in my newsletter that you should join.

My Annual Book Audit: 52 Books and the 52 Ways They Changed Me This Year

Read 10,000 books, travel 10,000 miles [to attain wisdom] - Ancient Chinese Aphorism

My Dad shared that proverb with me a couple weeks ago as we discussed my recent decision to quit my job to write a book. As Chinese sayings go, this one’s fairly straightforward: we read books to benefit from the wisdom of their authors so we are more prepared when we seek our own wisdom. He told me that while he’s nervous about my decision to burn cash for the foreseeable future, he’s comforted by the fact that I read a lot of books.

He's counting on the wise folks that write books to tell me when I’m making dumb decisions. Seems reasonable.

I usually don’t think I read enough. At the beginning of the year, I’d resolved to read a book a week (a dramatic increase from the ten or fifteen books I’d read the previous year). I wasn’t satisfied with certain aspects of my life and wanted to make some adjustments. I thought that reading the right books might give me perspective and help me build and break some habits.

My hypothesis was that these books would help me make small changes in the right direction and eventually sum to big, positive changes.

So I had this nice thought at the beginning of the year and then didn’t think much about it until this morning when I woke up and thought I should see how I did.

And for the first time I can remember, I stuck to a resolution! I actually beat it by two books. This year I read 52 books and each one changed my life a little bit.

So without further ado, all 52 books and the associated impact each one had on me.

(aside: what's the deal with default styling for html tables? Column width is all over the place)


Title Author Change
10% Happier Dan Harris Started recommending this book to people that both read and are struggling to meditate
Jim Henson Brian Jones Started searching for something I'd be passionate about like Henson was passionate about his work
Surely You're Joking, Mr. Feynman Richard P. Feynman Started to dabble more in things I find curious
I Am Malala Malala Yousafzai Stopped doing things for work that didn't have a positive impact on the world
Kitchen Confidential Anthony Bourdain Stopped ordering fish on Mondays and hollandaise sauce at brunch
I Come to You From the Future John Robert Heffron Stopped reading books with hashtags in the title
Creativity Inc Ed Catmull Stopped second guessing whether searching for something I was passionate was worthwhile

Favorite: Surely You're Joking, Mr. Feynman gr


Title Author Change
Monk and the Riddle Randy Komisar Started asking myself "what would it take to do this for the rest of my life" to judge whether I'm working on the right thing
Hooked Nir Eyal Started to skim books instead of reading every word if the insight is in a framework that's easily understood
Your Brain at Work David Rock Started to write down priorities for the day first thing in the morning
The 22 Immutable Laws of Marketing Al Ries Stopped reading books that are lists
Mindset Carol Dweck Stopped thinking of myself as "talented." Started to focus on how skilled I was at growing.
The Adventures of Johnny Bunko Daniel Pink Stopped worrying about losing sight of "the plan" because there's no such thing
The Hard Thing About Hard Things Ben Horowitz Stopped thinking that I had a clue when it came to being a good employee
Steal Like an Artist Austin Kleon Stopped worrying about being derivative

Favorite: Monk and the Riddle gr


Title Author Change
The Alchemist Paulo Coelho Started my search for meaning in work. Helped me trust my gut
The Tao of Poo Dirk McFergus Started practicing acceptance of the present moment
Gone Girl Gillian Flynn Started reading fiction again after years of reading only nonfiction. So good I read it at Coachella
The Rosie Project Graerne Simsion Started research to identify the best martial arts I should start to learn
The Beach Alex Garland Started to consolidate my posessions to live with less
The Catcher in the Rye J.D. Salinger Started to maintain childhood naivety in everyday life even if adulthood comes with an unavoidable loss of innocence
Ishmael Daniel Quinn Stopped believing in "the way things are" in work and education
Fear and Loathing in Las Vegas Hunter S. Thompson Stopped reading Hunter S. Thompson
The Stranger Albert Camus Stopped reading existentialist books (even though Camus did not self-identify as one)

Favorite: The Rosie Project gr


Title Author Change
Mindfulness Joseph Goldstein Started being kind of Buddhist
Man's Search for Meaning Viktor E. Frankl Started interpreting the world in terms of meaning
Zero to One Peter Thiel Started journey to build a "competitive monopoly" for myself
Catching the Big Fish David Lynch Started meditating again after a couple failed attempts
Everything is Bullshit Alex Mayyasi Started searching my brain for things to unlearn
Delivering Happiness Tony Hsieh Started seeking people and organizations with missions to surround myself with
Waking Up Sam Harris Started seriously meditating and unintentionally evangelizing
The Obstacle is the Way Ryan Holiday Started to embrace barriers as opportunities to practice skills required to overcome them. Pairs nicely with growth mindset
The Art of Learning Josh Waitzkin Started to embrace incremental learning by practicing the same skill every morning every day (writing, currently)
Eating Animals Jonathan Safran Foer Stopped eating red meat (e.g. cows, pigs)
Show Your Work! Austin Kleon Stopped reading books that are really listicles (fool me twice...)
Free Will Sam Harris Stopped thinking about the concept of free will because there's no point
Young Money Kevin Roose Stopped wondering whether I should have tried finance

Favorite: The Art of Learning gr


Title Author Change
Understanding Comics Scott McCloud Started drawing
The Design of Everyday Things Donald Norman Started to blame poorly designed systems instead of individuals for failures
Objective-C Programming Aaron Hillegass Started to build an iPhone app
Your First Meteor Application David Turnbull Started to build simple web-apps with Meteor
OmniGraffle 6 The Omni Group Started to choose one tool for each discipline I'm interested in to more quickly achieve unity with my tools. OmniGraffle is for wireframing
The Visual Display of Quantitative Information Edward Tuft Started to develop my own style guide for charts based on Tuft
Discover Meteor Tom Coleman Started to learn web development by learning Meteor
Don't Make Me Think Steve Krug Started to simplify all of my designs to just its core functions
The Elements of User Experience Jesse-James Garrett Started using the Garrett's framework to organize thoughts for any project requiring design
Resonate Nancy Duarte Stopped beautifying my presentations
iOS Programming Joe Conway Stopped building iPhone app
A/B Testing Dan Siroker Stopped prematurely optimizing things (like reading A/B testing books when I didn't know how to design yet)
Simple and Usable Giles Colborne Stopped reading "bite sized" technical books like this one to better spend time on more thorough technical books
Sketching User Experiences Bill Buxton Stopped thinking about design, development, and marketing as sequential with clear inputs and outputs
The Right to Write Julia Cameron Stopped worrying about quality of writing and started to focus on quantity

Favorite: Understanding Comics gr

Themes I noticed

This year was exceptional first for the sheer volume of books I read and second for the impact I allowed each book to have on me. I went into each book looking for something smart to learn from it that I could apply to my life. I'm not sure why I did this, but it's probably because for the first year in a long time, I didn't think I had all the answers. Now that the year is over, I see even clearer how few of the answers I have. 

Knowing how little I know is a very nice feeling! I don't have to worry about having an air tight plan and I don't have to worry about always being right or skilled. It means I don't have any other options but to read a book, walk a mile, and repeat.

Some themes I noticed as I was doing the audit: 

  1. Meditation: started and stopped several times throughout the year. Now I've gone for over six months without missing a day.
  2. Work: quit my job to write and self-publish a book. Solves working on something I'm passionate about, will have a positive impact, and helps me build a competitive monopoly.
  3. Creativity: enabling myself to make things without fear of judgement. Know that I'll get better over time if I practice diligently.
  4. Design and Development: built a foundation to start making internet things early next year, confirmed that I enjoy the process.
  5. Family, friends, relationships: nothing specifically on these topics, but have focused a lot on being mindful and compassionate, bringing my best self to my closest people. 

These observations might be the most encouraging evidence I've seen for focusing on the process rather than the eventual outcome. I don't think I'd have built defensible habits around any of these themes if I'd just woken up one day and said I'm going to do it. The big rewards come too slowly for my brain to register progress along the way. But when I focus on the process of slowly accumulating these positive adjustments--really just bi-products of reading and paying attention to the world--I don't worry about the ultimate outcome and then after a while I look back and there it is. 

Something to keep in mind as we make our New Years Resolutions. 

Happy Holidays!

I love talking about books and I'll pretty much read anybody's favorite books. What books have had the biggest impact on your life? What were your favorites from this year?

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Post-Manuscript Depression

I sent my editors a nearly complete first manuscript of Working Jobs on Monday morning and unceremoniously shifted my attention to the design, marketing, and selling of the book. After months of coaxing words onto the page, agonizing over structure, and battling my inner critic, I now had at least two weeks to focus on anything but the production of a manuscript. It felt weird.

Producing the manuscript was like training for a marathon or studying for a huge exam. It takes a lot of effort to make that initial commitment, but once the commitment is made, it’s just a daily grind. Wake up, grit teeth, grind. Repeat. Then you realize that you’re at the finish line and the marathon is over. You get up and turn in your exam and walk out of the lecture hall. A couple days later, you look back at it and squint a bit because you can’t quite believe that you actually did that.

I started to feel disassociated with my work. I woke up with anxiety, nervous that I’d wrote the whole thing with blinders on, oblivious to the fact that it was unreadable. I started to compulsively refresh my inbox for any communication from my editors like a student waiting for test scores to appear.

But then I just started to focus on the other things on my task list. I designed a couple of book covers that I felt happy with and started conversations with a few companies that were interested in giving away products to future readers of the book. Whenever I’d worry about the manuscript ever reaching a publishable level of quality I’d find solace in the fact that my editors were working on it instead of me.

Then, I looked through my manuscript for blog post ideas that I could use to drum up interest for the book. I picked out five or six of them and thought up natural destinations for me to share them (e.g. subreddits). And something miraculous happened… I remembered why I wrote Working Jobs in the first place: to share the stories of people trying to love what they do so that others wouldn’t feel alone in their own pursuit.

For the last couple of weeks I’d been so caught up with the uncertainty of leaving my job and the rush of finishing my manuscript that it’d become all about me. I needed to make my book good so I could sell copies and pay rent. Now, I remembered what had carried me through the whole process: the prospect that somebody that I’d never met might interact with something of my creation and make a great decision for themselves… a decision that would move them closer to reaching their potential and benefit the world.

This might sound a little cheesy but I’ll end this with a quote from Paulo Coelho.

And, I don’t know — why do you use this word cheese? You’re too cheesy? [laughs] Do I have anything about cheese? When you say [laughs], oh, he’s being too cheesy when [he] manifest[s] something that it is the most important thing that we have, we become very cynical. Probably this is is defensive. You know? And not natural defensive attitude, because you want to love, you want to share your love, you want to show your love, but you don’t want to be cheesy. So, you destroy everything.


This Week

Next Week

  • Complete first full draft of website
  • Add recommended reading to each chapter of the manuscript
  • Search for an illustrator or sketch things myself

Recommended Reading (storyteller's edition)

  • The War of Art gr
  • The Right to Write gr
  • Save the Cat! gr
  • Daily Rituals gr


How am I doing? Is this interesting? I know many of the ~hundred of you currently receiving this newsletter personally and I’m treating this like a one-directional penpal arrangement. Are there any topics that you’re particularly interested in? Any questions you want to ask me?

Any suggestions on any aspect of this project is so deeply appreciated. And thank you for reading.

This is Week 2 in the series I’m Writing a Book (each edition is published a couple weeks after it's written)

Get weekly reflections (just like this one) on the *Working Jobs* project in your inbox every Sunday

DIY Book Covers for $10ea with GIMP, Google Fonts, and Stocksy

The book designer's responsibility is threefold: to the reader, to the publisher and, most of all, to the author. I want you to look at the author's book and say, "Wow! I need to read that […] A book cover is a distillation. It is a haiku, if you will, of the story. - Chip Kidd watch his TED talk

People that create things know that in the early stages of creation, a focus on the aesthetics can lead you down a deep, dark, hole of procrastination. The writer who edits obsessively while writing struggles to write. The product designer who focuses on every pixel while prototyping the concept fails to spend the adequate energy on the bigger picture. The start-up that focuses more on their website and social media than developing their product and talking to customers ends up falling behind competitors focused on the fundamentals.

The would be author that spends too much time on a book cover laughably early in the process eats into valuable time better spent making the book itself better, or pre-marketing it so that it might eventually get read by someone.

You know what I say to that? Who cares. I enjoyed making these covers and it’s my book and I get to spend my time how I’d like so suck it. So what if I spent a couple days mocking up book covers. Point is, now that I’ve done it, if you or your friends ever need to do it, you can just replicate what I did.

Here are three designs that came out of the process: 

Nothing special, and the most recent version is already different from these original designs (way less selfhelpy thank God). But having something done and imperfect was exactly what I needed at this stage of the process.

The whole thing took some time because I had to learn some of the mechanics of doing this in the process, but if you follow what I did, you can have a couple mock-ups in an hour for your own book cover or poster or display ad or christmas card or whatever beautiful thing you’re making.

Here’s how I approached producing these designs:

  1. Asked myself what kind of emotional response I wanted from the reader
  2. Picked a color palette
  3. Selected a complimentary font-pairing
  4. Gathered a selection of images and illustrations
  5. Mix and matched until something worked

1. Eliciting the right emotions

My book is called “Working Jobs” and focuses mostly on loving what you do for a living. The easy answer here is to create something fuzzy and happy, warm and approachable. Something that says, “Hey there, are you a little lost? A little disgruntled? This is going to taste like warm birthday cake.” Warm images, fun round serif fonts, happy colors.

But I didn’t want to do that. I didn’t set out to write click-bait in the form of a book. My book was serious. I wanted to share brutally honest stories and iconic thought leadership, not feel-good guilty reading. I didn’t want my reader to buy the book and then hide it in a drawer. I wanted it to sit prominently on the coffee table (never mind that most of the copies will be ebooks).

I wanted art. So I looked for inspiration in art galleries and found this beauty

David R Prentice Moon Flag 2 1979

I realized I wanted motion, sophisticated colors, familiar shapes. I wanted it to elicit the calm of really well designed furniture.

2. Picking a color palette

I generally knew I wanted it to resemble “Moon Flag 2,” so I went to Fabrizio Bianchi’s beautiful color palette generator coolors.co, put in some of the colors and started generating palettes. The only significant change I made was swapping the navy blue from the Prentice to a pastel turquoise, because I wanted to lighter accent color to use for my web design.

The red was my primary color, the eggshell and grey would be light and dark background/text pairings, the turquoise an accent color, and the white would be a secondary color whenever red didn’t work.

This palette would serve as reference both the book cover and any visual design related to Working Jobs.

3. Selecting a complementary font combination

I’m actually quite bad with type, but I knew I wanted a sans-serif font for the header text and a serif font for the body text. Ideally, both fonts would come from Google Web Fonts because they’re free, well-supported, and easy to use in google documents and websites.

I already knew I liked Source Sans Pro for my sans serif font, so I just needed to find a nice, readable serif font to pair with it.

Honestly, I just kind of scanned Google’s web fonts at this point and picked Noto Serif because I knew Google used Noto in a lot of production projects for Android. If it’s good enough for Google production, it’s good enough for me.

If you’re looking for inspiration, check out femmebot’s beautiful Google Web Fonts Typographic Project.

4. Gathering Images and Illustrations

The quickest way to get graphic inspiration is to page through stock images that don’t suck.

My current favorite is Stocksy. I’ll just browse through a bunch of pictures, put the ones that jump out at me in a folder, and play around with them until I like one. When I decide to go with one, I pay for the rights and that’s it. Super easy, super cheap.

Stock images get a bad rep because of how laughably shitty the generic stock image looks, but there’s a new crop of stock images that look pretty dope. So I pay the stock image haters no mind.

I wanted something abstract and artistic, complementary with my color palette, so I picked a handful of pictures symbolizing work, offices, childhood, creation, and art.

5 Mixing and matching

I opened up GIMP (an open source photoshop alternative that I barely know how to use) and started to put text on top of pictures. I used a bold, all caps version of Source Sans Pro for the title, a light Source Sans Pro for my name, and a bold version of Noto Serif for the subtitle. I used either white or red for the header, and a grey for the subtitle and my name.

Picking a cover

I’m not sure which one will end up gracing the cover of Working Jobs yet, but I have a strong preference for the middle one that’s currently on the website. I’ll probably develop a few more when the publishing date nears and put it to a vote here. If you have a preference, let me know in the comments.

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What Happened to Man's Search for Meaning?

Ever more people today have the means to live, but no meaning to live for. - Viktor E. Frankl

When man first walked the earth, we asked ourselves how we would find the day’s sustenance. Next, we wondered how we would protect ourselves from the dangerous world around us. And as soon as we felt full and safe, we started asking ourselves why we were placed on the earth.

We begin asking why as children and continue to ask it periodically throughout our lives. It’s a question that has spawned and sustained powerful religious organizations as well as a multibillion dollar self-help industry. But it’s a rare person who feels a deep connection to their life’s purpose.

The promise of this kind of self-actualization drives our life’s biggest decisions. As children, we incessantly ask question about the world around us so we can understand how things work and how they relate to us. We begrudgingly go to class because our parents and teachers tell us we’ll have more satisfying lives if we learn the material. And we pay our dues at work, slowly climbing the corporate ladder to achieve some kind of 'American Dream' that will finally make us the envy of our peers and solve all of our existential issues.

Viktor E. Frankl, author of Man’s Search for Meaning and one of the most influential psychologists in history, believes that man’s relationship with meaning is the singularly most important relationship we have. After surviving life in World War II concentration camps, he dedicated his life to the study of meaning both in his clinical work and research. In one of his studies in France, he showed that 89% of people needed “something” for the sake of which to live. In another, he surveyed college students and found that their primary goal was “finding a purpose and meaning to my life.”

I think we can all relate. We’d love to find a purpose and meaning to our lives and live effortlessly, unburdened by the ambivalence of not knowing, in service of your life’s meaning.

Instead, we treat it like a teenager treats romantic love. We desire it from a young age, watching Disney movies and reading love stories, but will never quite know what it feels like until we experience it. With each new lover, we test whether our experience lines up with our expectations, but never really know whether our expectations are reasonable, or whether any lover will ever meet them. Until, for the lucky few of us, we fall in love.

Our introduction to work follows a similar pattern. As children, we dream about growing up to take on these heroic roles, idolizing figures that inspire us, hoping one day to feel the same kind of importance and purpose. As we enter the workforce, we inevitably feel a bit of a letdown, but aren’t sure whether what we’re feeling is what everybody else is feeling, or if we’re just being entitled millennials.

I’m curious about the experiences of everybody else. Did you feel let down by work? Did you feel like everybody was sharing that letdown or did you feel a bit alienated like I did?

Something I’m so grateful for since since sharing the Working Jobs project is receiving messages from old friends and new acquaintances (soon to be new friends!) sharing their stories from work. Stories of quitting and staying, stories of anxiety, fear, and love. Hopefully you’ll let me share many of these stories. They’ve had such a warm impact on me because—haha this sounds silly—but I was starting to take the entitled millennial thing personally. I didn’t want to be entitled or selfish but I also couldn’t stand working without purpose any longer.

This post is adapted from my forthcoming book, Working Jobs. If you haven't already, subscribe to my weekly newsletter to read more of the book as it comes out.

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