12 Month Reading Challenge: The Hard Thing About Hard Things Review

I’ve always considered myself to be a bit of a reluctant leader. As a college student, I became the de facto leader when it came to group hangouts, organization of sports teams, and even just campus lunchtimes. But I also knew I wasn’t really good at it, and during my time as an educator, I started to really understand my shortcomings. That’s why when I began Dudefluencer, I didn’t want to make the same mistakes as before, which led me to review The Hard Thing About Hard Things by Ben Horowitz.

On my journey as a first-time entrepreneur, I want to learn as much as I possibly can when it comes to starting my own business, self-improvement, and becoming a better leader. So along with my monthly 30-day challenges, I’ve also decided to read and review at least one business or self-improvement book a month while implementing their suggestions.

The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers is a straight to the point, no-nonsense look at Horowitz’s career, including plenty of discussion about his own mistakes in the business world. As someone who is always afraid of fucking up, Horowitz’s novel let me know that it will be impossible for me not to screw up, but it is essential to learn what screw-ups can really destroy a company.

The Hard Thing About Hard Things Review

If I were to compare Horowitz’s book to any other teaching book I know, it’d be Stephen King’s On Writing. Like King’s book, Horowitz opens The Hard Thing About Hard Things with around 75 pages of personal narrative to help set the scene and also establish a rooting interest for Horowitz.

The book opens with Horowitz at Netscape, and by page 15, starts his own business, Loudcloud. Throughout the novel, Horowitz manages to intertwine stories about the Struggle of becoming an entrepreneur and straight to the point pieces of advice. Horowitz establishes his credibility early on, and every word of advice feels like it is coming from an expert.

Not many writers can establish a personal narrative, self-help, and entrepreneurial guidance into one book, but Horowitz manages to do it well.

The Struggle is real.

I’ve only been writing for Dudefluencer for around five months, but there have been numerous times when I’ve felt doubt, imposter syndrome, and anxiety. Horowitz calls this “The Struggle,” or the moment when “you wake up to find that things did not go as planned.”

I quit my education career in June of last year, and after my numerous successes in the classroom, I thought it’d be easy to get another job. I figured, “Hell, I’ve got two Masters degrees, a variety of experiences, and awards from my time in Prince William County, I’ll have a job in two weeks.”

Two weeks passed, and I didn’t get an interview. A month passes, and I haven’t heard back from anyone. Three months passed, and my ego was shot.

Rachel sat down next to me and said, “Garrett, you’ll regret it for the rest of your life if you don’t try to do Dudefluencer full-time.” I believed her, even though I didn’t believe in myself.

Horowitz explains that every great CEO from Steve Jobs to Mark Zuckerberg went through “The Struggle,” and that it is reasonable to have those moments of self-doubt. “When you are in the Struggle, nothing is easy, and nothing feels right. You have dropped into the abyss and you may never get out. In my experience, but for some unexpected luck and help, I would have been lost.” There’s a correlation between how Horowitz describes the Struggle and depression.

Dudefluencer immediately struck gold, breaking thousands of hits our first two months. I told myself we will only keep growing. And then November happened. Our pageviews dropped tremendously and only got worse in December. I felt hopeless and lost. But two pieces of advice from Horowitz’s book helped push me through my first interaction with the Struggle.

“Don’t put it all on your shoulders.”

Being the only person teaching full-time creative writing in my district made me feel lonely. Of course, I had writer friends, and I had teacher friends, but none of them were writer-teacher friends. So a lot of my problems remained just my problems.

So when I started experiencing the Struggle, I kept all my insecurities and anxieties to myself. Horowitz tells readers, “You won’t be able to share every burden, but share every burden you can.” Being an entrepreneur can be lonely, but I am lucky that I have Rachel. Far more experienced in the world of content marketing and SEO, I consider Rachel to a be a superstar (and one of the best writers I’ve ever gotten the chance to read), so the fact that I can talk to her about my anxieties and fears about Dudefluencer is hugely important. I don’t feel as alone anymore.

But Rachel wasn’t enough: I started reaching out to my friends, Dave, Scott, and Tony. And like the amazing people they are, they responded quickly with invitations to hang out, plans for phone calls, and a patient ear as I vulnerably admitted to them that I didn’t have it all figured out. And it was okay because no expected me to.

I felt like I had a team of people to support me.

In Horowitz’s case, he called an all-hands meeting and explained the problems with the company, and “the team rallied, built a winning product, and saved my [Horowitz] sorry ass.”

“Don’t take it personally.”

Horowitz said, “Everybody makes mistakes. Every CEO makes thousands of mistakes. Evaluating yourself and giving yourself an F doesn’t help.” This level of honesty from a successful CEO is the kind of knowledge I desired while reading this book. Not every business owner has the capability to admit fault when it’s easier to blame someone else. But true leaders accept that they are at fault, accept that they will fail, and move on towards finding a solution rather than wallowing in their mistakes.

His advice reminded me of one of my favorite Youtube videos by Dave Morris, The Way of Improvisation. Morris explains the importance of letting yourself fail “because failing is easy, everyone can do it. The hard part is to be okay with that and let yourself fail.” The fear of failure is what keeps people locked inside their heads, and in business, it’s a recipe for CEO’s to avoid taking risks no matter how important they might be.

I’ve always been self-critical of myself and avoided taking risks because I knew where the safe path left me. Now, as the founder of Dudefluencer, I quit my safe teaching position, my secure retirement, my reliable monthly salary for a cause I believe in. I haven’t had a ton of opportunities to make mistakes, but I know I have already.

Making mistakes won’t be the hard part of owning a business, it’s accepting that you do and successfully moving towards a difficult solution.

Take care of your people.

One of the problems I had with my career as an educator was that I felt underappreciated. That sentiment isn’t unusual amongst the teaching population. All I wanted was from my superiors to recognize what was happening in the classroom and celebrate my students. At the same time, I understood that it was a difficult task as the administration was required to wear so many hats and serve so many different bosses.

Horowitz noted that as CEO of Opsware, he held one-on-ones with employees to measure their progress and check in on what’s happening. But when a manager had failed to conduct those meetings for nearly a month, Horowitz asked his dad for some advice and came to the conclusion that “the more I realized that while I had told the team ‘what’ to do, I had not been clear about ‘why’ I wanted them to do it.” And that realization impacted the way Horowitz interacted with his company and teammates from then on. He began to understand that one of the cardinal rules of being a great company is instilling a belief that “in good organizations, people can focus on their work and have confidence that if they get their work done, good things will happen for both the company and them personally.”

Horowitz understood that there needed to be a reason for employees to be invested in their workplace.

The other focus of developing a good workplace is to train your employees. Horowitz understood that employees need to be continually learning, and companies need to invest resources in developing new skills for employees. He said, “Managing the company is the CEO’s job. While you won’t have time to teach all of the management courses yourself, you should teach the course on management expectations…”

When I envisioned Dudefluencer, I wanted to recreate the college newsroom, where I got my start writing. I loved learning from veteran writers, and obviously, I loved teaching those skills to others. As CEO, I want to develop writing teams, eventually, editing teams, led by people with experience educating and mentoring. I believe that building up a group of people together is the best way to develop a successful company.

Manage your own psychology.

Horowitz opens the chapter, “It’s like the fight club of management: The first rule of the CEO psychological meltdown is don’t talk about the psychological meltdown.” From there, Horowitz breaks that rule and goes through the various techniques utilized to help his mental state while CEO.

One of the heaviest sections of the book is when Horowitz explains that being a CEO is a lonely job. Simply put, there are going to be difficult decisions that will need to be made: letting go of friends, laying off employees, or even shutting the company down. But no matter how many advisors, friends, or board members you have around, no one will have more knowledge about the company and the situation you’re in than you.

And being forced to make those decisions by yourself is why being a CEO is a lonely job. Horowitz suggests that leaders find friends that they can talk to (obviously they cannot make the decision, but it’s always nice to have someone around who can relate), writing everything out on paper, and to “focus on where you are going rather than on what you hope to avoid.”

But Horowitz last piece of advice struck me the hardest. When he asked other CEOs how they made the tough decisions or made it through difficult times, the great CEO’s always responded: “I didn’t quit.” At times, I felt like when I left education, I quit, I failed. And maybe I did? 

But being honest with myself, I’ve never quit on the one thing I’ve always believed in: I am a good writer. Since high school, I’ve been writing, and while I took a break in graduate school to get my education degree, I promptly picked it back up after moving to Virginia. And I’ve never quit. And I’ve never stopped believing that writing, my writing, can help people.

And as long as I still believe, there’s no way Dudefluencer won’t succeed.

Final Thoughts

I loved The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers. Horowitz isn’t the most eloquent writer, nor does he pretend to be. Instead, he writes honestly, providing enough backstory that his advice comes with evidence of his success. I’ve already taken some of his lessons to heart, and I believe that this book was the perfect starting point for my 12-month self-improvement reading challenge.

Have you read Horowitz’s book before? Did you enjoy it? What other business books would you like to see reviewed for the Dudefluencer 12-month reading challenge?