With Christmas break just around the corner, many of us are looking forward to seeing family, enjoying festive meals and decorations, and taking a few days off school and work to try and recover from the stressful year that 2020 has been.

But as a homeschool student, why not use some of that down time to better yourself, too? If you’re actively interested in entrepreneurship—or have a curiosity about what it is—then doing some reading on it over Christmas break will be time well spent. In this blog post, we’ll look at four of the best books for future entrepreneurs.

What is an entrepreneur, anyway?

In this blog post, we define entrepreneurship broadly—it covers everything from the founder of a Fortune 500 company to a “solopreneur” independent contractor who works with a handful of individual clients each day. Ultimately, entrepreneurship is about beating a path down the way less trodden, forgoing a seemingly safer regular job and career to try and create value in the marketplace on your own. In others words, hanging out your own shingle.

Some people might think of a typical self-employed individual as not being an entrepreneur, but we prefer the broader definition that lumps these individuals in together.

OK, on to the list. Happy reading!

1. How to Win Friends and Influence People by Dale Carnegie (BUY IT)

If you’re looking to read one book with timeless wisdom for interacting with people, make this the one. Dale Carnegie originally wrote this book in the 1930s, but the advice has stood the test of time. Why? Because people fundamentally never change. Much of Carnegie’s thinking in the book is based on the Golden Rule of treating others like you want to be treated. Some key takeaways:

  • The only way to get other people to do what you want is by making the other person want to do it.
  • Criticizing people often leads to resentment and anger, not lasting change. “Any fool can criticize, condemn and complain—and most fools do. But it takes character and self-control to be understanding and forgiving.” Instead, look to motivate through incentives.
  • Be genuinely interested in other people.
  • The expression you wear on your face is more important than the clothes on your back.
  • The best word in the whole world for people to hear is their own name.
  • Humility: “There’s magic, positive magic, in phrases such as: ‘I may be wrong. I frequently am. Let’s examine the facts.’”

While How to Win Friends and Influence People is not a business book per se, it’s advice is highly relevant to any future entrepreneur. Check it out!

2. The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future by Chris Guillebeau (BUY IT)

This book is a great read if you’re looking for tips on making a low-cost, low-skill jump into the world of entrepreneurship. Guillebeau shares wisdom on how to get going with a business that uses your existing passions and skill sets with start-up costs at or below $100. He also looks to coach you in a business that will generate at least $50,000 a year (roughly the average American salary), and ones that are easier to manage (fewer than five employees, and frequently the only employee being the entrepreneur).

Think of The $100 Startup as a basic primer in solopreneurship and microbusinesses. It’s a great place to start if you think this life might be for you.

3. Essentialism: The Disciplined Pursuit of Less by Greg McKeown (BUY IT)

Whether you choose the path of self-employment, full-on entrepreneurship by opening your own business, or the way of traditional employment, Greg McKeown’s short book Essentialism is a must-read. What I love the most about this book is its simple premise: “Essentialism is not about how to get more things done; it’s about how to get the right things done.” McKeown helps us differentiate between the essential and the nonessential and offers practical tips for living a life of disciplined essentialism.

“Only once you give yourself permission to stop trying to do it all, to stop saying yes to everyone, can you make your highest contribution towards the things that really matter,” he writes.

4. Good to Great: Why Some Companies Make the Leap and Others Don’t by Jim Collins (BUY IT)

Good to Great is just what it sounds like: Jim Collins and his team of researchers spent five years looking at companies that went from good (or worse) to something great, gathering the data necessary to develop some useful concepts and guidelines. They found that it’s more than just circumstances that make a successful company—it begins by choosing to adapt to new ways of doing business and having the discipline to carry out your plans. A major way to do that is by developing a healthy company culture with the right people, a concept the researchers refer to as getting the right people on the bus. 

Pick up a copy of this book and you’ll also learn about concepts such as the Flywheel. Essentially, this concept says you need to work really hard over time to get a product or service off the ground, which can entail developing something that serves a need (or want) and getting customers. Once you have these, you’ll still need to continue building relationships with your customers and assess how you can improve what your company provides, but it won’t be nearly as hard as it was when you first started.

Bonus: Other books to keep on your shortlist