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  • Writer's pictureKen Shaw

Warrior Wisdom: Lessons from Braveheart for Modern-Day Leaders

Updated: May 19, 2023

We all want and so badly need Freedom in all areas of our life, and we can have it. Better yet — we don’t have to die a horrible, bloody death to get it.

Audience: modern-day leaders who are struggling with being held back in aspects of their lives — personal, professional, physical, emotional, or spiritual. #leadership #freedom #courage #resilience #self-improvement

If only we could all smite our enemies with fireballs from our arse :-)

1. Introduction: Scotland’s Freedom Fighter

Haggis for Thought: If you’re not Scottish, your knowledge of William Wallace might be limited to Mel Gibson running around in a skirt, painting his face blue, and yelling about freedom in a suspiciously Australian accent. However, our man Wallace was much more than Hollywood’s interpretation. He was, in fact, a true symbol of Scottish resistance against English rule. He didn’t just fight for freedom; he gave it a bear hug and asked it out for a pint. Scottish 101: A little primer for those who thought William Wallace was a new whisky brand: Wallace was a Scottish knight who became a central early figure in the Wars of Scottish Independence against King Edward I of England. The man was a walking, talking symbol of ‘stubborn determination,’ a characteristic often associated with the Scots… and mules.

What is FREEEEEEDOM!! to us today? Most of us reading this are not literally fighting for our lives and freedom. I say most because I know a bunch of my Ukrainian friends are going to read this, and they literally are fighting for their lives and for freedom. All hail the warriors of modern-day Ukraine! These men and women are an inspiration and are fighting tooth and nail to throw Putin’s thugs from their borders, and they are winning in that great struggle.

I’d wager a barrel of fine whiskey that if Wallace were alive today, he’d be leading a battalian of Scottish volunteers on the Eastern-front of the war in Ukraine to see off the Russian thugs.

Ukraine today: it boggles the mind, that in 2023, we could have a real-life villain trying to take over a country in Europe by force. And yet, Ukraine has fought back with valor and is winning. Putin has seriously miscalculated. We are now seeing what millions of pissed-off Ukranian men and women are capable of, and it's phenomenal.

Corporate warriors: For the rest of us corporate types, what does Freedom even mean? Well, I can think of many ways we want to be free:

  • ✅ free from those modern-day mental monsters: anxiety, stress, and depression;

  • ✅ free from sleepless nights fretting about tomorrow, or wrestling with the demons of the past (and the demons come at night don’t they!);

  • ✅ free from the risk of heart attack and stroke! Yup that’s right boyo — the stress’ll kill ya;

  • ✅ free from conditional hope and conditional happiness — which comes from getting improperly attached (i.e. not free) to particular outcomes;

  • ✅ free from financial and technical debt that will eventually crush us;

  • ✅ free from false narratives, and limiting assumptions;

  • ✅ free from anger, irritability, and unwise actions;

  • ✅ free from cowardice;

  • ✅ free from judgmental thinking: ours and that of others

In short, we want to be free from shackles in all four dimensions of our life: physical, mental, emotional and spiritual. We don’t want to be “held back” in any of those domains. We don’t want adhesions that cause us physical or psychic pain (anyone who’s had adhesions in their muscles knows how awful they can be — and how terrific freeing them up feels). We don’t want to face any pain in these four areas of our life.

Wouldn’t that be bloody marvelous?

Taking a holistic approach to your well-being is a recipe for creating a formation of great strength, with each area re-inforcing the others, like rows of Scottish infantry ready to slaughter the lilly-livered British!

2. The Early Years: Young Wallace’s Lessons

Boy in Plaid: Wallace’s early years were not exactly a montage from an 80’s sports movie. There’s no record of him running up hills, punching slabs of meat (think Sly Stallone in the awesome Rocky montage!), or participating in competitive haggis eating. Wallace was a younger son of a minor noble, which meant he had all the status of a third-string quarterback on a high school football team.

Invisible Lessons: Some historians believe Wallace’s father was killed in a skirmish with the English when he was a boy, which was likely his first taste of English hospitality. This early experience possibly shaped Wallace’s views on freedom and independence, fostering a burning desire to ensure his people weren’t treated as the proverbial red-headed stepchildren of the British Isles. Lessons in Sarcasm: Of course, we mustn’t forget the important teachings of Mel Gibson’s rendition of William Wallace in the 1995 film “Braveheart.” Remember that scene where young Wallace returns as a man to his village and flings rocks with precise aim? Let’s just say, an early leadership lesson there: accuracy counts, whether in stone-throwing or decision-making! Remember, folks: freedom isn’t free, and neither are the lessons we can learn from our skirt-wearing, freedom-loving friend, William Wallace. 💡Hack yourself to level up: so how can we improve our accuracy in decision-making? I like to remember the old adage of “measure twice, cut once”. I.e. when I’m making a decision, and I think I’m ready to act, I try to take a beat, and then turn the problem upside down and ask myself two questions: “are there any other paths I could take that I haven’t considered, or that I’ve considered and discarded?”. And secondly: “consider the risk — if I make decision X, and then pursue action Y, are there any hidden risks lurking in the darkness getting ready to mug me?”. Only after I’ve answered both of those questions in the negative do I then move into execution mode (pun intended!). Doing this stops me from losing my head (pun again intended!). 3. The Battle of Stirling Bridge: A Lesson in Strategy

Strategic Genius or Lucky Guess?: Here’s where the plot thickens, like a good bowl of Scottish porridge. The Battle of Stirling Bridge in 1297 was William Wallace’s debut on the grand stage of history. Contrary to popular belief, he didn’t merely charge into battle, face painted, screaming, “They can take our lives, but they’ll never take our freedom!” Under the Bridge: The real story is that Wallace, along with Andrew Moray, used the narrowness of the bridge to their advantage. Instead of attacking head-on, they let a portion of the English army cross before ambushing them. It was like letting half a lion into your living room before slamming the door on its rear end. Unconventional? Yes. Effective? Absolutely. 💡 Hack yourself to level up: what are the lessons we can draw from this for today’s tumult? Create bottlenecks for life’s challenges and handle them one at a time. Don’t try and fight all your enemies at once. Don’t try to solve for your whole life’s problems at the same time. Narrow the field of battle, and knock down your challenges one at a time. That’s how you can beat overwhelming odds. 4. The Idea of Freedom: Wallace’s Driving Force Freedom isn’t just another word: If there was one thing that really tickled Wallace’s fancy, it was freedom. It was his coffee in the morning, his nightcap before bed, and his reason for putting his life on the line. A Catchphrase is Born: Mel Gibson might have given us the immortal “FREEEEEDOM!” cry, but Wallace truly embodied it. As a leader, he was driven by the idea of an independent Scotland, free from English rule. It’s a bit like wanting to move out of your parents’ house because they still treat you like you’re 12, except on a national scale. 💡 Hack yourself to level up: go back to the list from the introduction, and really ask yourself how many of those freedoms you currently enjoy? Print it out… and grab a red pen and mark them off for yourself. For the ones where you’ve got a big stinkin’ red X mark, do a root-cause analysis. Ask “why” 5 times in a row. I can’t sleep. Why? Because I’m worried about work. Why? Because I have a big meeting tmrw that’s stressing me out. Why? Because I don’t feel prepared. Why? Because I haven’t spent enough time reviewing my notes? Why? Because I had to take out the trash, cook dinner, and look after my kids. Well — that’s frickin’ OK isn’t it? Those are good reasons to not be chained to your desk. So be free of the guilt you are feeling, set aside those nerves, and get a good night’s sleep. You’re gonna perform better with 7 hours under your belt in any case! 5. Defeat and Resilience: Lessons from Falkirk Not all Sunshine and Roses: Now, Wallace wasn’t some invincible superhero. He didn’t stride around in a kilt, deflecting arrows with his bare hands. In 1298, the Battle of Falkirk served him a heaping slice of humble pie, and it wasn’t even gluten-free. Bouncing Back: Despite this setback, Wallace didn’t throw in the towel. He didn’t mope around, binge-eating haggis, chugging scotch whiskey (which I think he’d just call whiskey), and singing sad songs. Instead, he showed resilience, a quality all leaders need, because let’s face it: not every decision you make will result in a victory dance. Sometimes, you have to dust yourself off, learn from your mistakes, and plot your next move. Because, as we all know, even in defeat, there’s always a chance to yell, “FREEEEEDOM!” again. 💡 Hack yourself to level up: resilience is one super-power that Wallace (and all the Scots) had in abundance. We need it in our lives. Life is a distance race, not a sprint. Rudyard Kipling nailed it in his immortal poem If:

If you can make one heap of all your winnings And risk it on one turn of pitch-and-toss, And lose, and start again at your beginnings And never breathe a word about your loss; If you can force your heart and nerve and sinew To serve your turn long after they are gone, And so hold on when there is nothing in you Except the Will which says to them: ‘Hold on!’ If you can talk with crowds and keep your virtue, Or walk with Kings — nor lose the common touch, If neither foes nor loving friends can hurt you, If all men count with you, but none too much; If you can fill the unforgiving minute With sixty seconds’ worth of distance run, Yours is the Earth and everything that’s in it, And — which is more — you’ll be a Man, my son!

Kipling might have been sozzled most of the time, but he sure could turn a phrase. And he sums up the grit and determination we must aspire to, we’ve gotta channel our inner Braveheart and fill every minute with 60 seconds worth of distance run! 6. Guerilla Warfare: Innovation in Battle Tactics Think Outside the Box: Wallace wasn’t a fan of traditional warfare. He wasn’t about to line up his men on a sunny field for a polite exchange of arrows. No, he preferred the ‘surprise party’ approach. Ambushes, quick strikes, late-night attacks — that was more his style. A sort of “sneak up and yell ‘surprise!’ with a sword” kind of deal. Adaptable Wallace: This kind of innovative thinking is something today’s leaders could use a hefty dose of. Forget out-of-the-box thinking; Wallace was barely in the same postal code as the box. Whether you’re leading a country, a company, or a cub scout troop, remember: adaptability isn’t just about surviving — it’s about thriving. 💡 Hack yourself to level up: Epictetus wrote 2000 years ago that anything we do by habit or rote should be interrogated. As you find yourself being a corporate automaton, doing things on auto-pilot, try and catch yourself. Ask — am I doing this for good reason? What’s another approach? Am I approaching this problem or task with “boxed-in” thinking? What’s another angle? Then adapt. Change. Evolve. Be better every day. The grand canyon was carved from stone one drop of water at a time. Every day you can make choices that will make you a Natural Wonder as well. The fully actualized and free human being we all have a shot at being, that we call can be, one decision and one day at a time. 7. Diplomacy and Alliance-Building: Wallace’s European Tours The Scottish Ambassador: Despite his fondness for guerilla warfare, Wallace wasn’t all swords and battle cries. He knew when to sheathe his weapon and extend a hand (preferably not the one still covered in battle gore!). Global Networking, Medieval Style: After his defeat at Falkirk, Wallace took on a diplomatic role, trying to gain support from France and possibly even the Pope. Think of it as networking, but with more parchment and fewer business cards. He understood that sometimes, leadership means knowing when to ask for help — and offering a sturdy alliance in return. 💡Hack yourself to level up: do an inventory of the relationships you have that make you better; that make you stronger; that support you. Again — grab a pen and paper and draw your own little Charlotte’s Web, with you in the center. Nurture those positive relationships and build on them. Maybe schedule on your calendar talking to those folks each fortnight. Find more that are like them. In your inventory identify relationships that suck your energy and time and strength. Diminish these. Make yourself the center of a powerful network of positive people that can support you and teach you and stretch you, and come to your aid when the English Armies come raiding North! 8. Wallace’s Execution: The Price of Freedom

He might be dying, but he knew what he was dying for: FREEEEEEEDOM!!!! His voice was heard echoing around the nations and still today rumbling down the halls of history.

A Bloody End: Unfortunately, our plucky hero’s tale does not end with him retiring to a cosy highland cottage. Wallace was eventually captured and executed by the English in 1305 in a way that makes “Game of Thrones” look like a kid’s show! Freedom till the Last: Despite his grim fate, Wallace never wavered from his belief in Scottish independence. His final word (at least according to Hollywood) was — yup, you guessed it — “FREEDOM!” Leaders take note: dedication to your cause is commendable, although perhaps try to avoid getting hanged, drawn, and quartered in the process. 💡 Hack yourself to level up: Wallace’s demise is a reminder that in the end we will all face death and become nothing but dust and ashes. So what matters then? Well — it’s how we use the time that we have left. It’s the journey we take, the path less taken hopefully, the stops and tumbles along the way, and the way we deal with them. The destination is certain for us all: death. But how we get there? That’s up to us. 9. Wallace’s Legacy: Impact Beyond Death

More than a Man: Though his life was cut short, Wallace’s impact was anything but. He became a symbol of resistance, a beacon of hope for a free Scotland. His legacy wasn’t about the battles he won, but the spirit he embodied. Long-lasting Impact: To this day, Wallace is celebrated as a hero of Scotland. His life and his love for freedom continue to inspire, reminding us that a leader’s impact can far outlast their lifespan. As long as they remember to pay their library fines before they go. 💡 Hack yourself to level up: Stephen Covey talks in his book The Seven Habits of Highly Effective People about future tripping. It’s a cool thought experiment: pretend you’re at your own funeral, and you’re seeing what people say about you, and how they react to your demise. It’s a powerful exercise. What is your legacy going to be? What will you leave behind at the end? If we can free ourselves from all those encumbrances above, I’ve got to believe that I’ll leave behind people that miss me yes; but also a group of people whose lives were enriched by having me in it. I want to be remembered as a guy who lived with purpose and intention and did big things for those he loved. So with that in mind, I can ask myself “How today will I make the folks at my funeral proud of me tomorrow?”. Give it a try. 10. Conclusion: Applying Wallace’s Lessons Today Translating Kilts into Suits: Wallace’s story offers many lessons for today’s leaders. Courage, strategic thinking, resilience, adaptability, innovation, diplomacy, and dedication — these aren’t just qualities of a medieval Scottish knight, but characteristics of effective leaders everywhere. Wallace in the 21st Century: So, whether you’re rallying your troops for a company merger or standing your ground in a boardroom battle, remember Wallace. To bastardize Gibson’s speech from the 1st video above, when we’re dying in our beds many years from now — don’t we want to be able to roar with defiance that whilst our troubles and tribulations may have taken part of our lives — they never took our FREEEEEDOMMM! Wouldn’t that be grand laddie? And if all else fails, try painting your face blue and see if that helps. Just be prepared for some very confused looks :-) Thanks for reading, Ken


About me: I’m a software engineer by training and a software leader by profession. I’ve led two California-based SaaS companies as CEO, and am now back in my home country Australia. I’m passionate about tech & product & believe product management is the highest leverage activity a CEO can participate in. I’m here on Medium writing mostly long-form posts on topics I’ve got experience in, like #Leadership #Fundraising #Investing #SaaS, #Product, #Startups, #Offshoring. I’m on LinkedIn regularly — feel free to connect with me at

Shaw Investments: You can also learn more about what I get up to at or submit a financing proposal to us for consideration. We are early-stage tech investors, usually investing in companies with between $100k and $1M in ARR. We also invest in commercial real-estate. Reach out to me on

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