The Value of Difficult Conversations
“If you avoid conflict to keep the peace, you start a war inside yourself.” – Cheryl Richardson
We’ve all dodged a conversation we knew needed to happen.
Something uncomfortable. Something that wouldn’t go away on its own.
Maybe a colleague crossed a line or your boss was unreasonable. Maybe your partner brought up a past issue you thought was settled. You knew you should say something—but didn’t.
We always have a reason not to speak up. We rationalise it to ourselves yet delay or avoid it. But all we’re really doing is kicking the can down the road—and giving the problem more room to grow.
There’s that old saying: “The best time to plant a tree was 20 years ago. The second best time is now.”
The same goes for tough conversations. Yesterday was ideal. But today is the next best option—don’t let it sit until tomorrow.
The Power of One Conversation
In October 1962, the US discovered Soviet missiles secretly installed in Cuba—just 90 miles from Florida. The world edged towards nuclear war.
For 13 tense days, leaders scrambled for a way out. Formal talks went nowhere.
Then came a quiet meeting between US Attorney General Robert F. Kennedy and Soviet Ambassador Anatoly Dobrynin. Behind closed doors, RFK offered a deal: if the Soviets pulled their missiles from Cuba, the US would quietly remove its missiles from Turkey.
The Soviets wanted those missiles gone. The US didn’t want to be seen as backing down. So the deal remained private.
One quiet conversation averted global catastrophe—and a war like none seen before.
Making the Hard Call
In the early 2000s, Netflix founder Reed Hastings faced a tough choice: have a painful conversation that could end a friendship—or risk the future of his company.
Netflix was struggling. Streaming hadn’t started yet. His co-founder and friend, Marc Randolph, had been key in launching the company—but didn’t have the leadership skills to steer it forward.
Reed told Marc it was time to step down as CEO. He believed he could lead better.
Marc stepped aside. Reed took over. Today, Netflix is the largest streaming platform in the world, with over 300 million subscribers as of January 2025.
And the two men were able to remain friends as Marc respected Reed for what he did.
Take the Long-Term View
Being willing to have a hard conversation shows maturity. It shows you can zoom out, look at the big picture, and prioritise the long-term over short-term discomfort.
It’s not just about speaking up. It’s about how you do it—saying what’s true, in a way that helps, not harms.
“You don't have a right to say whatever you want. You have a responsibility to say what is true, in a manner that is helpful.” – Jordan Peterson
This week…
“People are trying to be smart—all I am trying to do is not to be idiotic, but it’s harder than most people think.” - Charlie Munger
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The latest post by Justin Welsh for his weekly newsletter: The Saturday Solopreneur
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An X post (here) by George Mack to remind us that we need not place anyone on a pedestal, in the end, there are no real adults around.
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For any Fantasy Lovers, I’ve just started “Wind and Truth: The Stormlight Archive Book Five by Brandon Sanderson.
I hadn’t realised it had come out so I’m a bit behind but I cannot recommend this series enough.
Book Recommendation…
Sam Walton : Made in America My Story
At the end of his life, Sam Walton wanted to pass on the lessons he’d learned over the years. As the founder of Walmart, he had built the world’s largest retailer from incredibly humble beginnings—outpacing rivals with deeper pockets and more experience.
In this book, he shares exactly how he made it happen.
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