Business and Life Lessons I learnt reading Diary of a CEO

If you plan on skipping the book, look up Bartlett’s Blue Slide and you might just change your mind

I love libraries, I love the smell of books, I spend hours at bookstores. Up until the past year, I had spent all my life always carrying a book. I’d read every free minute I got. Didn’t matter if I was at work, school, doctor’s clinic, travelling, or on a date. I’d never be found without my book. All this changed when the only person whose literary recommendations I seriously take started supplying me with more ebooks than I could keep up with reading and all so slowly but surely I moved towards keeping books on my iPad. Definitely still missing touching books, but I have to admit I love the freedom of getting to carry options to read without the shoulder strain.

When this enabler of mine, in not just this but many other habits too, told me he loved Diary of a CEO so much that he was going to get a physical copy so he could make notes, I realised I had to come out of my hiatus from reading business self help books and check it out.

This book had been built up to me so much that the extremely opinionated me suddenly finds herself completely unable to rate it. While I didn’t find the book as ground breaking as I had started to hope it would, it still left me with quite a lot of very important thoughts. While some laws in the book are very basic and even seem cliched, some are put so well that even if you’ve heard and ignored them before, you suddenly feel them embedding themself deep inside you.

Many times I found Steven’s voice condescending and self proclaiming but understanding the deep impact of his work, it felt deserved. I didn’t find myself wanting to hate him. This I feel was quite a well achieved delicate balance. Steven’s voice though is another topic people can write pages on. His words are militant calls to action. They are direct, they are sharp, they are confident and they make you sit up and take cognisance. It is hard to ignore his rules, his advice no matter how sleepy you are, even if you’re a bedtime reader like me.

I couldn’t wait to write this review because I couldn't wait to discuss some of my favourite parts of his book. While most have more to do with work, one thing I resonated a lot with was in the first few pages, within Laws of Self. Something small but significant was put casually but made me feel so validated. Steven talks about how people felt their mortality deeper than they had before during COVID and how this brought about a health paranoia. I am someone who’s been struggling with this despite being fairly healthy and though I had started to talk about it lately, never had I felt more confident and normal than I did reading his words. Our world I see is witnessing a health revolution whether it is with biohacking or AI trackers or advanced tests and I do hope more people talk about it especially in the space of working since until the world at large starts prioritising mental and physical health in the work arena, we wont be able to sufficiently upturn the upheaval startups have brought upon with their endless work glorification.

As someone who struggles with wanting to be right, Steven’s advice on how not to start a debate by disagreeing also made me take notice. He puts it in a way that doesn’t make you feel like you’re loosing power and so helps you consider executing it in a way you might not have thought of before.

There are a lot of rules about standard start up culture like awe and shock, amaze and daze, piss people off, dare to disrupt, etc and these do get annoying for someone who’s been reading this genre a lot. But I don’t hate the book for it as I do understand that these are important pep talks for someone for whom this might be the first of this category of books they pick up. I was just slightly bored reading them. I felt they weren’t written with as much commitment either as some of the other rules were.

If you’ve read my post from the start till here, and have been paying attention, you probably would be wondering why I’m so fascinated with a blue slide. ‘Useless absurdity will define you more than useful practicalities’. This is one of Steven’s wonderful rules from the book, borrowed from his personal experience. I could feel the child like excitement and happiness with which he wrote this rule and though I’m too timid to go straight ahead and try it, it’s a very fun part of the book to read and would definitely prompt you to hit google search. It was definitely the first rule that directed me towards the internet to read more about him, his company, his work, and his blue slide of course.

A student of sociology, I understand how important human psychology is, and even though eventually this is not the part you probably take away remembering from the book, I feel it was done with quite sophistication. Steven talks about the Goldilocks effect which basically is just our tendency of choosing the middle option of falling between 2 extremes but the way he writes it amuses you about your own habits as we have all been victims of this, Steven included. He makes you understand how doing that basically makes us human all the while teaching us how to be more conscious of this bias.

Comfort zone is our biggest enemy. We all know this. We all fail to disrupt our stability to experiment. I am guilty of it and while I am still struggling with it as I write this post, Steven makes a very compelling case about the art and triumph of failing repeatedly. It makes you less scared of failure and gives it a one night stand quality - you know it’s bad, you know you’ll feel less of yourself after it - but you still realise it’s probably the best way to let loose, and just go for it so you can be better skilled at your craft.

If you’re not a young college drop out entrepreneur building something nobody around you can understand, a lot of times you might feel like you’re not reading the right book but I think this one rule in particular was quite great for people involved in family businesses. Steven talks about how older more structured companies struggle to grow fast because they become too bureaucratic and how younger counterparts of the older executives of these companies outperform due to their ability to execute quicker and with less red tape. I think this was a huge nod to the youngsters joining old established firms and definitely something they could use to bolster their perspectives in the next family meeting.

I recently started my own company and while it is not a revolutionary idea, rather consulting in a traditional field, it is still challenging and needs the correct principles to get it stable and growing. While at points I felt like I was struggling to understand how I could best use certain rules, some rules I feel were gospels every executive needs to know no matter how big or small their enterprise is and so these were my favourite. He talked quite a bit in the last section about building your ideal team. And while rules about building a cult like following were valuable, I felt less identified in those stories. I benefitted from reading about hiring and analysing hires. Steven talked about how while hiring the first few people we must understand that these people will dictate the culture of your company. He advised to judge every employee by imagining how we’d feel if every person in the firm was like them. The minute I read this, I could picture the faces of the people I work with and in my head was so clear about the direction I needed to take my company in when it came to building my team. In today’s age of solopreneurship and lean organisations, a lot of us struggle to delegate and thus struggle to find people we like for our teams. His advice on team building was for me the highlight of the book.

We all have heard that we must lead by compassion, that we must know how to motivate our team members, that we must have great people skills to know how to get what we need done by whom. So Steven’s last rule wasn’t surprising but his illustration of Sir Alex Ferguson’s management of Manchester United was fascinating and I sing high praises about it because I read it without skipping a word despite not being a sports fan so I can only image how gripped sports enthusiasts, especially footballers would be reading this part.

Becoming a Plan A thinker, leveraging the power of progress were also noteworthy rules. I particularly like that Steven’s anecdotes comprise of various athletes, entrepreneurs, and some regular people who survived through catastrophes with their grit so you don’t feel like you cannot connect as there’s something in it for everyone.

While Steven talks highly of his podcast in the book, it didn’t make it to my favourites list despite the fact that I am a huge podcast listener and am always on the lookout for new content. But his book was definitely an insightful page turner for me. I will give another listen to few more episodes of his podcast before I cast a verdict, but for me the book, is definitely a big thumbs up.