🙃 How To Be Agreeably Disagreeable

More lessons from poker🃏

Hey You! How’s it going this week? 🙂

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You know how sometimes the most sensible thing to do is to agree and be compliant? It makes life easier. It keeps you out of trouble. And it avoids conflict. Well, that’s how I felt last week, but I just couldn’t.

My client had given me the job to re-write the landing page copy. The brief: a focus on safety whilst maintaining the brand’s tone and personality.

Excited to flex my copywriting muscle, I got to work.

By mid-week, I forwarded my ideas over to the founder to make sure she was happy.

A few hours later, she replied, “I want to encourage you to think more about the ‘urgency of safety’ in the copy.”

Disheartened by the reply, I did the most sensible thing I could think of - I took the next day off and had a BBQ.

I mulled it over. I uhm’d. I ahh’d. I let the word “safety” sizzle away in my brain as I grilled wings on the barbie.

But something in my brain kept pushing back.

It wasn’t because my ego was bruised. It was because this line of copy my client wanted violated every bit of her brand’s personality and tone. Her brand was light, optimistic, and playful. But the copy she wanted conveyed a dark and ominous tone.

Agreeing to the feedback would’ve been a disservice to her and her startup.

So on Thursday morning, I sent her an email voicing my disagreement.

The rest of Thursday felt like hell.

“What was I thinking sending this email?! I’m going to get fired. This is my first client too! Who am I to even push back?”

My head drowned in anxiety. I paced back and forth in my room. And every time I refreshed Gmail, my heart skipped a beat.

At 10 PM, I received the following email…

“Proceed with the first copy you sent over.”

Phew.

It turns out that pushing back and disagreeing with a client’s feedback comes with the copywriting job.

To Agree Or Not To Agree?

I had always thought I was an agreeable person. But last year, my therapist pointed out that I’m quite the opposite - I disagreed with her of course.

After that revelation, I reflected on what people have told me in the past.

What my ex-girlfriend said 3 years ago when we first met:

“You don’t really care what other people think. Well it’s more like you accept people will have different opinions to you and you’re open to hearing it but you know what you want.”

According to a close friend:

“You love a good debate. You like to pick apart my argument and challenge my thinking all the time.”

According to the Big Five/OCEAN Assessment:

Big 5/OCEAN assessment was taken 6 months after my therapist pointed out my disagreeableness (most likely affected the test).

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Also, my mum is a very disagreeable person, so it’s baked into my genes.

I don’t do it to be a dick. I do it because poker taught me to have a sound thought process, which can come across as disagreeable.

But it was in poker where I learned to disagree like a diplomat.

Every week my study group would conduct a ‘hand history review’. We shared the hands we played. Critiqued them. And debated the best possible strategy.

If you thought someone was wrong, you had to point it out and give a solid reason why.

Differences in opinions can lead to the conversation getting more heated. Your inner dictator sometimes takes over and you resort to remarks like “you’re a f*ckin' idiot” to try and get the point across.

Calling people names makes people defensive, and they stop listening. The result: you get nowhere.

I know it sounds obvious not to hurl abuse. But in this social media era, a gentle reminder is sometimes needed. It has become too easy to attack, belittle and condemn others without consequences. Each side blames the other for not listening.

It’s essential to disagree in poker and in life because confirmation bias can easily hijack your brain. Disagreeing well is how you improve your thinking and let ideas flourish.

“You must not fool yourself - and you are the easiest person to fool.” - Richard Feynman

Disagreeing Starts With Listening

I’ve found the most effective way to disagree with someone starts by listening to them.

To make someone feel heard, all you need is this one sentence: “So what you’re saying is… [repeat what you think they said].”

You then address their points with sound rationale. Use phrases that don’t undermine them or belittle their intelligence.

Phrases like:

“Have you considered…”

“I think/feel…”

“It seems/sounds/looks like…”

“What if you took this approach…”

Disagreeing well isn’t about convincing others. Inform - sure. Discuss - definitely. But only they can convince themselves. It’s a fool's errand of trying to impose my will on you.

In his memoir Greenlights, Matthew McConaughey recounts a lesson he learned in Africa.

After an afternoon of racing camels in the Sahara Desert, Matthew and his two African friends, Ali and Amadou, sit down for dinner. Out on the veranda of the hotel restaurant, a young lady of the night came strolling through.

“Oh this is not good. This is a Muslim woman and this is not the Muslim way. You do not go and sell your body, this is a disgrace, she should not be doing this,” said Ali.

“Well, it is not for any of us to judge what someone should or should not be doing. We do not know her particular circumstances, what she does or does not is not for us to say,” countered Amadou.

The two men go back and forth. The conversation grew more animated and passionate.

Having enough of their ‘argument’, McConaughey interjected - He agreed with Ali.

But Ali snapped back at McConaughey,

“It’s not about right or wrong. It is ‘Do you understand?!’”

The point Ali is trying to make to McConaughey isn’t about who’s right or wrong. It is to be open and meet others halfway. It’s about listening. It’s trying to understand others.

You may not agree with someone, but you can always choose to understand and disagree with kindness.

—Jason

P.S. I’m happy to hear if you disagree with this post.

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What I’ve been listening to:

🎙 Consistently Good Not Occasionally Great - Nick Bare x Chris Williamson: A talk on finding success in anything you’re trying to achieve.

What I’ve been watching:

📹 Climbing with Alex Honnold: Magnus Midtbø collaborating with the legendary Alex Honnold. Warning: sweaty palms will occur.

What I’ve been reading:

🧾 The Rise of the Internet’s Creative Middle Class: Food for thought as someone who is part of this class.

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