If you like to read biographies to find the ideas that extraordinary people have used to achieve great things, then you want to read this book.

“Can you recommend a book for…?”

“What are you reading right now?”

“What are your favorite books?”

I get asked those types of questions a lot and, as an avid reader and all-around bibliophile, I’m always happy to oblige.

I also like to encourage people to read as much as possible because knowledge benefits you much like compound interest. The more you learn, the more you know; the more you know, the more you can do; the more you can do, the more opportunities you have to succeed.

On the flip side, I also believe there’s little hope for people who aren’t perpetual learners. Life is overwhelmingly complex and chaotic, and it slowly suffocates and devours the lazy and ignorant.

So, if you’re a bookworm on the lookout for good reads, or if you’d like to get into the habit of reading, this book club for you.

The idea here is simple: Every week, I’ll share a book that I’ve particularly liked, why I liked it, and several of my key takeaways from it.

I’ll also keep things short and sweet so you can quickly decide whether the book is likely to be up your alley or not.

If you’ve already read a book that I recommend or have a recommendation of your own to share, don’t be shy! Drop a comment down below and let me–and the rest of us “book clubbers”–know!

Lastly, if you want to be notified when new recommendations go live, hop on my email list and you’ll get each new installment delivered directly to your inbox.

Okay, let’s get to this week’s book: Alexander the Great by Philip Freeman.

alexander the great book review

If you like to read biographies to find ideas, models, systems, habits, etc. that extraordinary people have used to improve their lives and achieve great things, then you want to read this book because Alexander the Great wasn’t just one of the greatest military geniuses of all time, he was also, to quote the author, “…perhaps more than any other man in history, the absolute embodiment of pure human ambition with all its good and evil consequences.”

In short, Alexander was a man who conquered much of the ancient world simply because he could, and for that reason, he’s one of my personal favorite characters in history. Here’s a guy who took about fifty thousand troops and went on a truly epic journey: he marched them thousands of miles to the ends of the known world and led them to victory in scores of sieges, battles, and skirmishes, including many where they were out-numbered several times over, and ultimately toppled the Persian empire and created what is still one of the largest kingdoms ever. You just can’t help but admire someone who dared such great deeds.

Now, some people are going to be “triggered” by my horrible, violent words and whine about how Alexander was nothing but a maniacal, genocidal, mass-murdering thug LITERALLY HITLER, and to them I say…you’re stupid.

Yes, he killed a lot of innocent people, but writing him off as a psychopath is far too simplistic. He was a man of his times and no better or worse than pretty much every other general in the ancient world, including celebrated figures like Hannibal and Caesar.

Furthermore, as Freeman explains in the end of this book, a compelling argument can be made that Alexander’s escapades laid the foundation of Western culture.

Specifically, in later years, the Romans were so fascinated with Alexander’s exploits that they developed an intense interest in Hellenic philosophy and literature and disseminated far and wide, from the sands of Syria to the shores of Britain. Then there’s the fact that the New Testament and most other popular early Christian literature was written in Greek, which was almost universally spoken as a result of Alexander’s conquests, enabling it to go “viral” in a way that simply couldn’t have happened were it to have been written in Jesus’ native language, Aramaic. It’s very possible, Freeman says, that without Alexander, Christianity would have remained a local phenomenon and we would be living in a very different world today.

Anyway, regardless of how you feel about what he did, I promise that you can benefit from learning about Alexander’s life, and out of the several biographies I’ve read on him, this is my favorite.

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My 3 Key Takeaways from Alexander the Great


“Toward the end of the march, when officers and men alike had all but given up hope of escaping the desert alive, some scouts found a small spring with only enough water to fill a single helmet. The patrol was so thankful that they had found even this that they brought it before Alexander, who was as thirsty as anyone. As wretched as his own state was, however, he knew his men were suffering even more. Therefore, just as he had done in the desert crossing in Bactria four years earlier, Alexander refused to drink when his army could not. He took the helmet of precious water and poured it on the ground in full view of his army. To the parched men, for their king to share in their suffering in this way meant more than the water soaking into the sand. They were so heartened, says Arrian, it was as if they had each drunk every drop that he poured on the ground.”

My Note

Alexander proved again and again that he wouldn’t ask his men to do anything that he wouldn’t do himself, he even went as far as intentionally enduring as much pain and suffering as they did, and often more. He conducted himself as a first among equals in a body of free men, not as a divine lord to be worshipped with elaborate rituals and pomp.

These are hugely important leadership lessons. I’ve written and spoken about this before but it bears repeating: if you want people to work hard and make sacrifices for you, you have to work at least as hard and make sacrifices that are at least as difficult and meaningful as what you’re asking of them. Just being smart or nice or charming isn’t enough.

Simply put: if you want to lead people, you have to be someone worth following.


“Alexander, however, did not fall into an easy sleep that night. He knew that the Persians outnumbered him at least two to one and that they had chosen a field of battle that played to their strengths. In a broad plain, the tens of thousands of horsemen drawn from every corner of the empire would easily stretch beyond his front lines and would certainly outflank him, enveloping his infantry until every last soldier was cut down. Or they could mass into an unstoppable wedge and force their way through his infantry. He had to think of a way to break through the Persian lines with his own cavalry and attack Darius directly. If he could kill the Great King or even drive him from the field, the Persian forces would collapse. But with so many heavily armored cavalrymen on the Persian lines extending beyond his own front line on both the right and left, it seemed an impossible situation. Then, sometime in the night, Alexander had an idea—a brilliant, daring, absurd idea. From that point on, the king slept peacefully. When Alexander’s officers arrived at sunrise the next morning, they couldn’t believe the king was still in bed. They didn’t dare wake him, so they ordered the men to all have a good breakfast. Finally, with the sun rising in the sky above the mountains to the east, Parmenion at last entered Alexander’s tent and called to him loudly two or three times before the king opened his eyes. The indignant old general asked how he could be sleeping so soundly as if he had gained a victory when the battle was still ahead. Alexander only smiled and said, “Why, don’t you know we’ve already won?”

My Note

Alexander always looked at difficult and even seemingly impossible situations differently than everyone else, even his best generals. He believed that nothing was truly impossible–that there was always a way out or through and onward–and that explains why he was willing to make monumental gambles again and again in his campaigns.

What I personally took away from this little anecdote is just how powerful that sense of forward motion is. Alexander viewed even the biggest obstacles and predicaments with a sort of contempt, as if nothing could really stop him from achieving his objectives.

There are many examples of this throughout the book, and another that stands out is an instance where Alexander and his army were attempting to take a city whose massive walls and formidable defenses turned out to be too great for his siege engines. What to do?

Well, Alexander noticed that the river flowing through the city exited the walls through a narrow channel. Maybe it was large enough to squeeze through and sneak into the town? It turns out his hunch was right; it had just enough space for him to shuffle through, so he arranged to lead a small group of soldiers into the channel and under the walls while his main force assaulted the front gates to distract defenders. Once inside, Alexander and his men ambushed the guards, opened the gates, and took the city.

The point is this: if we could learn to look at our own troubles in the same way as Alexander did, then we could be far more effective in all aspects of our lives.


“Once he had regained some of his strength, his officers began to chide him that his performance on the wall was a brave but foolish act for a king. It was not the job of a commander, they said, to risk his life in such a way when there were plenty of men in the army who could do the same thing. Alexander did not know how to tell his friends that for him such actions were an essential part of being a king. Faced with such criticism, he walked out of his tent into the camp. A grizzled veteran from Boeotia in central Greece who had heard about the rebukes of Alexander’s companions approached him. The man looked the king straight in the eye and said just a few words in his rural dialect—’Alexander, brave deeds are what true men do.’ The king embraced the old soldier and considered him a friend for the rest of his life.”

My Note

Some context here. This time, Alexander was attacking yet another city, and this time it belonged to one of the fiercest tribes in the Punjab region of India, the Malli.

The Indians had already lost several battles with the Macedonians and were making their last stand in the strongest of their fortresses. Alexander’s soldiers tried to find a way into the citadel but couldn’t breach the walls, so he grabbed a ladder and scaled the wall himself, followed by three of his men, and then fought his way through the defenders and jumped into the city and continued fighting alongside his bodyguard and attendant. Meanwhile, his army was going berserk, frantically trying to gain entry to the stronghold before they lost their king. Inside, Alexander was struck by an arrow in the chest, and he continued to defend himself until collapsing from blood loss, with only two men and their shields to protect him from the rocks and arrows raining down.

Finally, the Macedonians shouldering the gates shattered the wooden bar holding them shut, and then burst through just in time to save Alexander’s life. They brought a litter to transfer him to a nearby ship for treatment, and in a final display of grit and glory, the king ordered a horse instead, clambered onto it, and rode through his ranks to reassure them that he wasn’t going to die.

The takeaway is the final beat in this story. Why did he insist on taking such risks? Because that’s what true men did, and that’s the type of person he wanted to be.

Now, whether you agree with that statement or not is neither here nor there, because there’s a deeper significance to this story.

These days, many people’s actions are mainly dictated by what they want to have–the things and experiences that they think will make them happy. Decades of psychological research has conclusively proven that this is a horrible plan that is more or less guaranteed to backfire, but we’ll save that for another discussion.

The same research indicates that a much better way to go about living is first deciding who we want to be–what fundamental and guiding principles matter most to us–and then figuring out what we need to do to embody those values and become that person.

For example, in my case, my core values as a person include achievement, commitment, consistency, creativity, education, enthusiasm, and responsibility, and I consciously use these principles to guide me through my life. I want to be able to confidently say that, through my actions, I’m the type of person that values those things most. As a result of this, while I’ve definitely had my share of ups and downs, I’ve also been to keep my life on a generally upward trajectory by making a lot more good decisions than bad, and I expect things to continue improving so long as I stay true to who I want to be.

If I were to abandon those principles though, and start living for the types of things that most people fantasize about–money, fame, physical pleasure, and the like–then I would become the type of person that I really have no respect for, which would most certainly lead to my downfall. I keep this in mind when tempted to go astray and it has helped me maintain a pretty even keel.

Have you read Alexander the Great? What did you think? Have anything else to share? Let me know in the comments below!