One of the great pieces of advice I was once given by a university Professor, is that you should rarely be ashamed of failure because failure is often the evidence that you’re aiming at something worthwhile. That advice ran completely contrary to much of what I was taught at school, which insisted upon limiting risk and making ‘sensible choices’. I think there’s wisdom in managing risk effectively, but the way to manage risk is not to avoid it, but instead to take the risk out of an otherwise risky situation.

This is where books are invaluable. If you’ve ever made a decision which turned out to be poorly calculated, in all probability it could have been avoided if only you knew who to listen to for the right advice.

When you read a book on, like these 6 of my personal favourites, you’re listening to the accumulated wisdom of some of history’s greatest risk-takers and risk-managers. If you follow in their footsteps, you may find that you’re able to aim at something profoundly worthwhile, and actually achieve it.

1. How to Win Friends & Influence People in the Digital Age by Dale Carnegie Training

Dale Carnegie authored his original international bestseller How to Win Friends and Influence People in 1953, and since then it has sold over 15 million copies worldwide. This is an updated version which brings the same ideas into the context of the digital age in which we live – a word which Carnegie could never have anticipated.

Human beings are essentially relational. We need meaningful interaction with other people and for that interaction to be effective it must be consistent with the social rules which govern human relationships.

The digital age has undoubtedly made it harder to be influential outside of the virtual environments we live within. However, rather than being a domain of meaningless interactions, it presents us with a social environment just like any other. Using the same principles as Carnegie’s original book, the authors break down all the habits you need to adopt in order to build effective friendships online. This book will present to you the etiquette to adopt in order to win over your competition and to open people’s minds to the message you want to deliver.

This should be on the bedside table of every entrepreneur.

Read How to Win Friends & Influence People in the Digital Age.

2. Thinking, Fast and Slow by Daniel Kahneman

Daniel Kahneman, winner of the 2002 Nobel Prize for Economic Sciences, is undoubtedly one of the most influential and thought-provoking psychologists of the generation. In this book, he explains the two systems which govern much of our mind and which can make or break the way our lives unfold: our fast and intuitive thought processes, and our slow and rational thinking.

Kahneman breaks down the effects that teach type of thinking has in terms of our mentality, confidence, teachability and success. He does this by revealing the ways in which our minds fall foul of error and prejudice, as well as providing the practical techniques you can use to develop slower and smarter thinking.

Having read this book, you will know how to make far greater decisions at work, in your home life and entrepreneurial ventures.

Read Thinking, Fast and Slow.

3. The Lean Startup by Eric Ries

Building a business has changed beyond recognition in the past 20 or 30 years. It’s no longer about defining a business plan, searching for a heft loan and executing the plan to the letter. Those old ideas just don’t work for the vast majority of new ventures.

In his book, Eric Ries explores the techniques that entrepreneurs should use in order to effectively manage the risks of an early-stage business and lead to its success. His widely applicable ‘lean’ approach is being adopted all around the world, by defining the way that new companies are built.

In reading this book, you’ll discover how you can identify exactly what your customers are looking for. You’ll learn to build testability into everything you do and figure out where and when you need to adjust your focus in order to adapt before it’s too late.

This book will help you build effective innovation into the very heart of your startup.

Read The Lean Startup.

4. Start With Why by Simon Sinek

Why do some companies succeed and other fail? How can some businesses hit the nail on the head over and over again, while others are just one-time hits?

Start With Why is a unique book by one of the most influential mentors among young entrepreneurs today. Simon Sinek analyses a number of cultural leaders, such as Martin Luther King Jr and Steve Jobs to discover the common thread that ties their cumulative successes together. The answers in the title – they all started with why.

Sinek explains how businesses can move past knowing merely what they do and how they do it, and arrive at that far more fundamental question of why?

Only in understanding why we do what we do will it be possible to build a vision about how your business can make a positive mark on the world. When you start with why you will inspire creativity, motivate action and set your startup on a direction that leads to genuine change that is resilient to the changing marketplace.

Read Start With Why

5. Rich Dad Poor Dad by Robert Kiyosaki

This is a fantastic go-to book on the plain realities of financial stewardship.

Kiyosaki tears down the widely held myth that becoming wealthy is the product of earning a high income and instead suggests that the key is to invest your income into assets that work for you. This is the kind of knowledge taught implicitly by wealthy parents to their children, but which is absent from financial education in our schools.

This book breaks down everything you need to know about effective financial management in a clear and readable way, so that you’re able to maximise your ability to allocate resources towards the things that you care about, in the long term.

By no means least among the principles which govern the mindset of the successful entrepreneur, is that building a wealth-creating asset is at its heart. Your business is very much something you create, but which once mature is no longer dependent on you – it can generate income without your intervention.

Read Rich Dad Poor Dad.

6. Deep Work by Cal Newport

Technology and the internet has bred a generation of workers who spend considerable amounts of energy fighting interruption.

We are now raised with constant connection to a host of people and business all fighting for our attention. Whether it’s those noisy open-plan offices, the never-ending email inbox or the ‘ping’ from our smartphones, finding the mental space to think and focus can seem like a losing battle.

Cal Newport explores the concept which he calls ‘deep work’. He recognised that constant interruption has the effect of making our work shallow as we are only ever able to skim the surface of our workload rather than getting to the heart of what’s important.

In this book, you will learn how to adopt methods for removing distractions and achieving the state of focus which too many people have forgotten even exists.

If you’re committed to building or growing your own business as a freelancer, or business entrepreneur, developing the ability to practice deep work is one of the best decisions you could make in this distracted world.

Read Deep Work.