Read this if you want to be "an interesting man"

In 1951 David Ogilvy was creating advertisements to sell men's shirts for his client ‘Hathaway shirts’

But after 18 failed ad campaigns nothing seemed to be working and the client was running out of money.

Then Ogilvy had a bold idea.

On his way to the photo-shoot he stopped at a dime store and bought a $5 eye-patch.

He tossed the eye patch to the model in the photo-shoot that day and asked him to wear it in a few photos.

When the images came back Ogilvy knew he’d struck gold.

The eye-patch transformed the image from a 'product photo-shoot' into a 'story'

What people thought when they saw these images was this:

Who is this man? And how did he lose that eye? Was he in the war? Is he a spy?...

They were intrigued.

The ‘Man in the Hathaway Shirt‘ ad was a huge success and Hathaway became the second-largest shirtmaker in the U.S.

What does this have to do with masculinity?

The man in that ad seems…interesting.

A man with stories.

A man who has NOT lived a vanilla life.

What about you? Do you consider yourself interesting?

You don’t have to be a spy or wear an eye patch to be considered an ‘interesting man’

There’s an easier way

But its going to sound basic so stick with me'

Here’s one way to be an interesting man:

Learn to ask better questions

I’m talking about the art of communication which is probably not something your father taught you.

But it's something every man should know.

Communication is a huge topic that would take more than one email to cover of course.

But the fastest way to level up is to start asking better questions.

Here’s a simple example of a situation you experience every single day:

“How are you?”

“Good. How are you?”

“I’m good too”

“That's good”

Did you see what happened there?

NOTHING HAPPENED

No connection. Just a moment filled with dry small talk because of a dead end question.

Try asking something different instead.

Something specific.

It doesn’t really matter what you ask as long as it's not the cardboard flavored version of a question above.

For example:

“You look happy what were you doing before this?”

or…

“Oh you look like you’ve got a little spring in your step. What did you eat for breakfast?”

You’ll get a better answer.

They will start talking and opening up a little more.

Boom. You just made a connection.

Of course this is just a simple example for an everyday situation.

But it's powerful. And when you start to ask better questions in other areas of your life?

You connect more with people. People start perceiving you as interesting. And you start getting more opportunities. With relationships, women, career…everything.

Start saving “good questions” for each area of your life from today onwards.

General questions like the one above. But also dating questions. Questions for work. Questions for mentors. etc.

Yes, I’m suggesting you keep a question bank.

Here’s a few links to get you started…

🔥 Curated links to help you find better questions:

• ​HOW to start asking better questions​ - advice from Tim Ferriss, who has a wildly successful podcast where he interviews the top performers in all aspects of life

• ​A guide to asking better questions - My First Million Podcast​ - This short and sweet podcast is a great intro to this topic.

• ​The best questions to ask a mentor​ - a Tiktok video. Impress your mentors; don’t bore them.

• ​Better questions to ask on a first date​ - that are NOT “what are your hobbies” or “what do you like to eat?”

• ​5 questions to avoid boring small talk and become more charismatic​ - A Tiktok video that is great for introverts

That’s it for today.

- Alex

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