Eight Books That Helped Shape My Career

Simon Holden
10 min readApr 16, 2020

Given this unique opportunity in 2020 to spend a bit of time reflecting, I have been thinking back to the books that have influenced me over the 30 years of my working life post university, 21 of which have been spent in Financial Services Technology. I have discovered or been recommended these books at various points along that journey, and whilst I might not have been ready to absorb all of them earlier, I certainly would have benefited had I been able to. These are the books that I have bought as gifts multiple times for colleagues and friends since. I thought it would make a good first foray into the world of writing on Medium.

It is an eclectic mix and no doubt a reflection of my personal idiosyncrasies, preferences, weaknesses and biases. However, if you manage teams, work in a large organization or just if you are thinking about your framework for lifelong learning and development, then I think there will be something for you here. I hope you find it useful and look forward to the feedback and some other recommendations.

The 7 Habits of Highly Effective People — Stephen R. Covey

This was the first book to raise the idea in my mind of putting continuous thought and effort into making myself and my teams more effective. I think prior to that I thought that just working as hard as I possibly could on what was right in front of my face, and trying to be smarter than everyone else would do the trick! I think its 7 maxims are timeless and can be applied to all aspects of life and work. I am amazed at how Covey’s themes come up repeatedly in the literature, and you will see some of that shortly. The seven habits are:

Private Victory — Managing Yourself

1. Be Proactive

2. Begin with the End in Mind

3. Put First Things First

Public Victory — How to Work with Others

4. Think Win/Win

5. Seek First to Understand, Then to be Understood

6. Synergize

Renewal — Keep Building Your Skills

7. Sharpen the Saw

The Organized Mind — Daniel J. Levitin

Working at the nexus of Technology and Financial Services for over two decades, I have frequently found that the amount of information flowing at me is overwhelming. Turning information into knowledge, managing the limitations of my own understanding and memory, keeping on top of important tasks, and managing ongoing learning have all been challenging at times. As many of us do, I have evolved numerous systems and hacks, both mental and technical, to enable me to cope and I’m pretty pleased with where I’ve landed. I can keep the most important things in my head, have the ability find detail quite quickly, and find that I rarely drop important tasks. However, getting there involved a long series of trial and error experiments. When I picked up this book a few years ago, I was stunned to find practically everything that I had found out the hard way (and more) laid out in print. I recommend this to anyone who thinks about those aspects of self-organization and development.

This book is a tour de force that covers how the mind works, the history of memory and information processing and then applies that to different areas of modern life: home, social world, time, business etc. It finishes with a look to the future and what our children might need; as the father of two teenagers this is something I think about a lot given how much more information they are assailed with than I was at their age.

The Mind Map Book — Tony & Barry Buzan

Mind Maps are one of those things that I wish I had known about when I was at school, and I’m very glad to see my kids being taught these today both as a way to capture study notes in a succinct, visual and therefore easy to recall way, and also how to excel at creative thinking.

I have been using them for 10+ years by hand and also in software for both of these purposes and find them outstanding. At one point when I had a particularly diverse job, I even used a mindmap as my to-do list as well, with multiple levels of categorisation being critical to reducing the diversity to a manageable level.

Buzan covers much of the same material of how the brain works as Levitin but focuses more on what makes things memorable. Mind Mapping is something that can draw a chortle from those unfamiliar with them, but ask around and I guarantee you will find a hard core of dedicated and passionate advocates who, like me, consider them to be a critical tool for creative thinking and for capturing and enabling easier recall of knowledge.

Why We Sleep — Matthew Walker

Eminent sleep scientist Matt Walker opens this book up with an assertion that most of the developed world is in the grip of a lack of sleep epidemic, with two thirds of adults failing to get the recommended eight hours of nightly sleep. He then proceeds to lay out a research-backed view of the severe damage this can do to health and wellbeing: vulnerability to disease/longevity, impairment to cognitive ability, memory, judgment and reaction time, littering the book with facts that will shock you along the way e.g. more people are killed on America’s roads every years from micro-sleeping at the wheel than driving under the influence of alcohol.

After I read this book I began polling friends and colleagues and realised, in a very unscientific way, how widespread this problem is and how many of us are suffering some of the effects of chronic sleep deprivation. It’s fair to say that since reading this I have significantly changed my sleeping habits, valuing it on a par with diet and exercise in its importance to health, and actively trying to limit permanently extended working hours in the teams that I work with. Persistent long hours are one of the most toxic corporate cultures that one can encounter, and whilst I accept that they are occasionally necessary, I think this book clearly demonstrates how short-sighted and ultimately counter-productive they are.

Give & Take — Adam Grant

Success is often characterised as being down to a combination of hard work, talent and luck. In this book Grant focuses on a fourth, oft-neglected, factor: how we approach our interactions with other people. Every time we interact with another person at work, we have a choice to make: do we try to claim as much value as we can (a taker), or contribute value without worrying about what we receive in return (a giver)?

He debunks the classic binary split between takers as winners and givers as losers. He also tackles the middle ground of matchers who carefully calculate what they are likely to receive in return.

Grant’s philosophy is not naive though, and he articulates how one should spot a taker and walk away, avoiding “the three major traps that plague givers..of being too trusting, too empathetic and too timid”. He highlights that givers often make up the ranks of both the highest and lowest performers in an organization, with the “sucker” givers being the latter. It’s key to learn how to spot “agreeable takers” and once you’ve spotted a taker adapt behaviour to being a matcher, whilst also not mistaking a disagreeable exterior for a taker when actually a giver might lurk beneath.

Central to the book is the idea of paying it forward, with the successful givers being those who engage in continuous small acts of kindness and generosity, with no thought to immediate return. This is especially powerful when the act costs us little or nothing but can be significant to the other party.

The book is full of outstanding examples, none more so than that of Abraham Lincoln, which encouraged me to read Doris Kearns Goodwin’s ‘Team of Rivals’, an incredible book that would make my top 10 in many categories.

I believe the giver skills of networking, collaborating, evaluating and influencing can be fundamental to creating highly functioning teams and to operating in a large organization. Moreover, when givers succeed it creates a ripple effect of goodwill around those with everyone “rooting for them”, as opposed to the sour taste and bruises left by the successes of a taker.

TED Talks — Chris Anderson

Chris Anderson is the head of the TED talks program and this wonderful book pulls together his many observations of the different speakers and styles that he has seen over that time. He starts from the premise that there is “no one way to give a great talk” and offers the experiences as a “set of tools” to help you make the right choice given your style, abilities, the material and the audience. As well as a wealth of great examples drawn from many talks (which you can then immediately go and watch!) what also appeals to me about this book is his emphasis on the role of public speakers as story tellers. I think this is something that is far too often lost in the corporate world today, resulting in turgid, dry and frankly boring content that appears to tick all the boxes but fails to achieve the outcomes because it doesn’t engage the audience. Whatever your style and abilities as a public speaker, I think you will be able to find insights and tips here that will help you improve.

Simply Brilliant — Fergus O’Connell

I have spent the latter half of my career mostly operating at scale across large organizations, often in the execution of big programs of work across hundreds of people and systems spread all over the globe. My learning has definitely been empirical but O’Connell’s book is a beautifully simple capture of what I believe are the core things you need to get right to make large projects work well. Most of the projects I work on these days are Agile in some shape or form and I still find these themes as relevant as ever, although Agile perhaps tries harder to build them in from the ground up.

Seven timeless principles in a very quick to read book:

1. Many things are simple. Shun complexity and seek simplicity.

2. Know what you are trying to do. This is Covey’s “Begin with the End in Mind” principle.

3. There is always a sequence of events. Working with some view of a possible sequence of events is key — not as a tool of prediction but of understanding inter-dependencies, challenges and story telling.

4. Things don’t get done if people don’t do them. Know who is supposed to be doing this and what else they are working on.

5. Things rarely turn out as expected. How about the anti-fragile (see next book) program?! We rarely seem to get good news in a program so how should we think about this?

6. Things either are or they aren’t. What does done really mean and are we looking closely enough to understand? Or said another way, “don’t ever give me another finger in the air percentage complete ever again”.

7. Look at things from others’ points of view. We need to understand and appreciate all angles to lead effectively.

Anti-Fragile — Nassim Nicholas Taleb

As someone who has spent most of their Financial Services career working in and around Risk Management, I have always been drawn to probability, randomness and asymmetry of risk. I could have included either ‘Fooled By Randomness’ or ‘Skin in the Game’ from Taleb’s Incerto series of books as both were also hugely influential for me, but I think Anti-Fragile makes more relevant points on managing our working and professional lives. Also, much of his narrative is poignant given where we find ourselves with Covid-19, which is testing our anti-fragility to the limit ( Taleb has written something about this on Medium).

Taleb recognizes and indeed embraces the inherent randomness, chaos and stresses of our environment as being at the very core of what defines enduring systems, capable of surviving low probability but high impact “Black Swan” events. He lays out a kind of ultra-resilience that is truly profound, drawing on biology and evolution along the way. His definition of anti-fragile is anything that has more upside than downside (with the reverse being fragile). Moreover, he argues that antifragile systems have survived and triumphed over fragile systems because of volatility, randomness and stressors, and to remove those will weaken them and by implication, allow more fragile systems to emerge. He prizes the old and tested and encourages the experiencing of small mistakes to make the large ones less severe.

Warning, Taleb is not for everyone. His opinions are at times controversial — e.g. “if nature ran the economy, it would not continuously bail out its living members to make them live forever” — and he writes with an extraordinary level of self-belief that some might consider arrogant. He rails against the suppression of randomness and volatility in education, politics, the economy and our health, and in particular top down interventions by people with no “skin in the game” (the title of the last book in the Incerto). However, I find many of his ideas to be unique and supremely important in how to bring risk thinking to all aspects of one’s work and personal life.

There are a few other books that came close to making the cut: ‘Factfulness’ by Hans Rosling, ‘Good to Great’ by Jim Collins, ‘Drive’ by Daniel Pink, ‘Crucial Conversations: Tools for Talking when Stakes are High’ by Kerry Patterson and Joseph Grenny, and ‘The Undoing Project’ by Michael Lewis.

Please do explore these books and I hope they prove to be as inspirational and useful to you as they did to me.

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Simon Holden

Software Engineer of 35+ years experience; 20+ years in Financial services. Interested in all things Comp Sci, Tech Education, Leadership, Diversity & Inclusion