I stopped learning.

A few weeks ago I took some time to perform a retrospective over the past year, 2016. The act itself intimidated me, and filled me with fear. Fear that I would see flaws in my decisions so large that might be crushed with a burden of guilt, unable to continue leading my company. Unable to provide for my family.

Once I identified that fear, I knew it was a festering wound on my subconscious, reminiscent of my not-too-distant past and a full set of wisdom teeth that similarly haunts me. Festering wounds must be opened, cleaned, and closed properly, or risk loss of limb, or death. It was time.

My self-evaluation began with a simple task: rank the year’s top 3 successes and 3 biggest failures. I opted to start with the good news to gain some momentum. Always look for the momentum.

What followed was a few hours of hard truths, large and small wins, and net-zeros. I had managed to not ruin everything forever, and that was my largest takeaway. Not much to be proud of. I had also struggled with some difficult health issues all year, which took their place as a carefully placed asterisk on the ledger of my year’s efforts.

The specifics of what I uncovered that evening are not the takeaway for this article. Perhaps another. Instead, I’m focused on something the spotlight revealed. Among other things, it uncovered a blind-spot so large, so humbling, that I dropped everything to fix it.

I had stopped learning.

Not only was I not learning, and this is worse mind you, but deep down believed I knew everything I needed and was equipped with all the tools necessary to succeed. What a fool I had become. Winging it through life, playing the victim card. It was time to take up my education again.

Let’s be clear, I’m not talking about the Stack Overflow code and design how-the-heck-do-I’s that us web folk live and breathe on a daily basis. I couldn’t survive in this industry without staying current on critical pieces of tech. I’m referring to my personal and business education above and beyond the technical skills I apply to the tasks at hand.

I had been functioning like a technician (to borrow from The E-Myth) instead of a leader. Ignoring the experience of smart and successful titans of industry, those that paved the way before me and took to time to share their knowledge, is foolishness at its core.

And so I read. It was the holidays, work scaled back to slow drip to let us fill our days with families and opportunities to relax. At every opportunity I read, and read, and then I read some more. I stayed up late, got up early, and read in the bathroom. Don’t pretend you’ve never done it.

My iBooks account grew. Sanderson, Lynch, and Brown were steadily pushed down the screen by an incoming tide of authors like Kiyosaki and Fried, Newport and Cuban, Zinsser and Voss.

I highly recommend this reading position. It’s very comfortable.

In the span of 3 weeks (which brings this timeline current) I read 8 books, and am deep into 2 more. I took notes, weighed contrasting opinions, and discussed ideas at length with close friends. I made plans and immediately put them into action. I began to right the sinking ship. It was an 80's training montage, except the music was soft, the lights dim, and the unmoving scenery only punctuated by the subtle turning of digital pages.

I changed. My company changed. Even if I was the only person who knew it. It was drastic, radical, and powerful.

I learned how to command my day instead of survive it. How to build assets, gain momentum, negotiate, work smarter, and write more gooder. The re-learning has only begun, and I’m already a new person.

So what did I read that caused me to change almost everything about the way I work and operate? I’m glad you asked.

My Self-Guided Curriculum

I’ll be as brief as possible on the details because summaries of all these books abound, each more well written than mine. Instead, I’ll just tell you why I read it, and why maybe you should too.

Rich Dad Poor Dad

My first undertaking was a quick and enjoyable read. Rich Dad Poor Dad by Robert Kiyosaki. My reasoning was, I’m in this software game to make money after all, so this book was a natural place to start.

I had read it back in college, but very little of it stuck. This time, it was like a series of lightbulbs flipping on in my mind. Even after years of following Dave Ramsey’s principals in money management, there is much left to learn about fundamentals.

Robert tells his life story on what he learned from his two father figures, his Rich Dad and his Poor Dad. There are lessons on building assets, cashflow, the mindset needed to find opportunities, and many other aspects of personal finance that everyone should read. I’ll probably re-read it every year or two.

If you take one thing away from this book, it’s this:

Assets put cash in your pocket, liabilities take cash out. Your house is a liability. Go acquire some assets.

Deep Work

If forced to pick just one title from this list, pick Deep Work by Cal Newport. The most drastic changes in this phase of my life are coming from this book. I’ve quit social media, begun radically planning and scheduling my days, embracing boredom, and retraining my mind in a way I thought wouldn’t be possible in today’s society.

It has become my competitive edge. If you want to compete with me, you’ll need to read it too.


Rework by Jason Fried and David Heinemeier Hansson is one of several great books by the founders of Basecamp (formerly 37 Signals). This one didn’t blow my mind because I keep up with their blog, Signal v Noise, but I still highly recommend it for anyone running a product/services company. Improve process, productivity, culture, and your product itself while you’re at it. It’s delightfully logical and counter-cultural, two concepts that usually make me smile.

How to Win at the Sport of Business

Mark Cuban is not the best writer, nor do I subscribe to his particular method of success (work 24/7/365 and if you can’t do that try 18/7/365), but I enjoyed the book anyway. It’s a collection of Mark’s edited and updated blog posts from over the years. I heard there were gems in there, and I found some. Like this one:

Bottom line is this: If you are adding new things when your core businesses are struggling rather than facing the challenge, you are either running away or giving up.

When this sunk in, I shelved not one, but two plans I had only just put in place. I don’t run away, and I don’t give up.

Never Split the Difference

I heard Chris Voss on the Entreleader podcast and immediately bought and plowed through the book. Chris was the FBI’s chief hostage and kidnapping negotiator for many years. He developed a powerful toolbelt of skills that actually worked, all with the highest of stakes on the line.

Could you imagine if a hostage negotiator chose to split the difference? “Yeah, send out 5 of the hostages and feel free to kill the other 5. Cool?”

This book is often regarded as the modern evolution of Donald Trump’s The Art of the Deal. It’s not pages full of brain hacks and tricks, it’s a deep dive in to the emotions and systems of logic (or lack thereof) that drive human’s decision making processes. Each chapter begins with a gripping hostage negotiation which becomes the backdrop for each tactic. It’s fascinating.

The only downside is I don’t negotiate things very often. Reading it gave me an itch, and I’ve scratched some odd places trying reach it.


Jason Fried and DHH from Basecamp/37 Signals are back at it again, this time on the topic of remote working. Wilderborn is already a 100% remote company, so more than half the book was preaching to the choir, but I found several solid ideas that I plan to implement when I can.

If you run or work at a company that is against remote working, this book will challenge you. In a good way.

The Elements of Style

I had been covering only business and money to this point and decided to switch gears. Time to brush up on my writing skills.

William Strunk’s handbook on grammar is thorough and compact. In fact, it’s so short, its entirety is contained in the iBooks sample. It’s 47 pages of hard rules you should know. Read it once, reference it forever.

Perhaps you’re thinking, “but Jack, surely this information was on the internet!” I’m sure it is, but there are ads and distractions on the internet. No thank you, I’m done with those.

On Writing Well

All of these skills and plans are rendered worthless if they can’t be communicated. This next book is dedicated to improving your non-fiction writing game. William Zinsser stripped away the fluff, set rules for clarity, and sharpened my discernment for the nuances of the English language.

After 7 books, I knew I wanted to write again. It had been too long since I’ve covered anything other than Statamic. This book served as paint stripper for layers of cliche, tired metaphor, and cruft that had built up the walls of my mind. It got me ready. Not perfect mind you, but ready.

And now here I am, trying to write well and sharing my experiences with you. It took more than 140 characters, as well it should. The takeaway? Don’t be an idiot. Go and learn.

What are you reading?