Welcome to issue #37 of The Gents Weekly, a newsletter for the modern man.
New issues every Monday. Brought to you by the men of Gents Journey — Dean Bokhari, Stephen Seidel, and Matt McManus.
ENDS TOMORROW
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📝 THE MESSAGE
A timely piece from the gents.
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A comfort challenge
by Dean Bokhari
Halloween is around the corner and spooky vibes are in the air — which is why today’s issue of The Gents Weekly is on stepping into fear, rather than running away from it.
Sometime around 2010, I read a book called The Four Hour Work Week by Tim Ferriss - a business book about creating high-leverage products that allow you to make money from anywhere while living life on your own terms.
It was one of the first books I read when I got started building businesses of my own.
And it’s absolutely worth reading.
But I’m not here to talk about business today.
After every section of the book, Ferriss shares what he refers to as a “comfort challenge” - an action or exercise to help you apply the ideas he’s sharing.
I’ve forgotten about most of his comfort challenges, but there’s one I still remember to this day…
It was about forcing yourself to overcome social anxiety - by lying flat on the floor in a high-traffic public space for 30 seconds before standing back up and pretending like you did nothing weird.
Yes, seriously.
The logic behind it is to leverage exposure therapy principles to desensitize your nervous system to the fear of judgment and embarrassment.
So I decided to give it a shot.
I went to a nearby mall, by myself, and started looking around for the right place to try Ferriss’ comfort challenge…
Then I spotted one of those fountains you used to throw pennies in at the mall as a kid:
It was kind of a busy day.
People were strolling in and out of stores and casually walking past the fountain.
As I approached, I saw a kid toss a penny into the water.
Nostalgia.
I circled the perimeter of the fountain once, nervously thinking about whether to do it or not.
I was procrastinating and putting it off.
“Okay man,” I told myself. “Don’t be a bitch. Just do it.”
Then, as my heart was beating out of my chest, I took my position:
I laid flat on my back on that dirty mall floor, right in front of the fountain, and started counting to thirty.
Guess what happened?
Absolutely nothing. People just continued strolling along.
Most people didn’t even notice me.
Before laying down, I noticed an old man sitting on a bench in front of the fountain eating a pretzel.
Once I was on the floor, I remember seeing him peripherally, he stood up and sort of leaned over from a distance - peaking over to make sure I was still alive.
I had my eyes open and a polite smile on my face.
“28-mississippi, 29-mississippi, 30-mississippi”
I stood up and looked around.
A mall cop was slowly making his way toward me.
I gave him a nod and a wave 👋 — and then I just walked away.
It’s hard to say how many different ways I’ve benefited from trying this comfort challenge, but here are a few:
First, the nerves disappeared almost immediately after I lay on the floor—teaching me that most things aren’t nearly as scary as you think they’ll be once you work up the courage to do them.
Striking up conversations with people became effortless.
Approaching women got a lot easier, too.
Confidence went up.
It also helped me care a lot less about what strangers think of me.
All in all, that comfort challenge was a major win for me as a man - and all it took was thirty seconds on the floor in front of a mall fountain.
Now, I’m going to challenge you to do it too.
Here’s how:
Find a busy public place. A a sidewalk, Barnes & Noble, a coffee shop, anywhere.
Lay flat on the floor for 10-30 seconds. You can lie on your back or stomach. Just make sure you’re by yourself, and surrounded by enough strangers for it to qualify as a “busy public space”
After counting from 10-30, stand back up to continue your day as if nothing happened.
Do not explain yourself to anyone who stares or asks questions. After you’re done, just get up, smile, and carry on with your day.
Yes, the whole thing will feel awkward at first.
But you’ve got a hell of a lot more to gain than to lose by trying it out.
Side effects of this comfort challenge include (but are not limited to) the following:
Social anxiety is crippling for men everywhere, this helps you crack it.
You’ll realize many of your concerns are fake or harmless. So many men are worried to speak up or break social norms. Like it’ll have some sort of catastrophic impact on their lives. Laying down on the floor for 30 seconds helps you realize that oftentimes, your worst concerns are usually nothing more than a few strange looks from people you don’t know… And that has zero impact on your life.
It also trains you to detach your internal state from external validation, making it easier to take risks, pitch big ideas, or come face-to-face with rejection in your personal and professional life.
So try it this week.
There’s no better time to test your courage-muscles.
— Dean Bokhari
Co-founder, Gents Journey
📰 THE MOMENT
Sh*t that’s happening now, ICYMI
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This Week’s AI Prompt: Courage
Truth is on the other side of fear.
I learned that at ten years old when my childhood friend encouraged me to hop a fence. I was terrified. My legs felt like jelly. Every part of me said no.
But the second I got on the other side, I knew something had shifted. I could hop fences for the rest of my life. Not because I suddenly had superpowers. But because I’d proved to myself that the fear was bigger than the thing itself.
That’s what this is about.
Not climbing mountains or quitting your job or making some massive life change. Just the small fears. The small fences. The things you’re avoiding that, if you just pushed through them for five minutes, would change your relationship with yourself.
THE PROMPT:
Copy everything below and paste it into ChatGPT or Claude:
Help me get on the other side of the fence. I'm not looking to conquer huge fears—just the small ones that are quietly holding me back.
Help me:
1. Identify the small fence (What are you actually avoiding?)
- What's something small you've been putting off?
- What's a conversation you're dreading?
- What's an action that makes you anxious but isn't actually dangerous?
- What would take five minutes but you've been avoiding for months?
2. Figure out why you're afraid
- What's the actual fear underneath it? (Rejection? Failure? Judgment? Looking stupid?)
- How big is the real danger vs. how big does it feel?
- What's the worst that actually happens?
3. Realize the fear is bigger than the fence
- Once you do it, how will you feel?
- What will you know about yourself on the other side?
- How many times could you do this if you knew you could?
4. Make the move this week
- What's the one small fence you're hopping?
- When are you doing it?
- What's your proof that you did it?
Here's what I'm avoiding: [Be specific]
Here's why I'm afraid: [What's the real fear?]
Here's what happens if I just do it: [Paint the picture]
Don't let me overthink this. Help me see how small the fence actually is.
WHAT HAPPENS NEXT
The AI is going to help you separate the fear from the fence. It’s going to show you that most of what you’re avoiding isn’t actually dangerous, just uncomfortable.
By the end, you’ll have:
A clear picture of your small fear
Understanding of what you’re really afraid of
The vision of what’s on the other side
One fence to hop this week
WHY THIS MATTERS
Courage isn’t the absence of fear. It’s doing it anyway.
And it starts with small fences. With the things that make you uncomfortable but won’t actually hurt you. Once you hop one, you know you can hop another. And another.
That’s how you build a life where you’re not avoiding things. Where you’re moving toward them.
Run this prompt. Find your fence. Hop it.
Drop the small fence you’re hopping this week. Let’s see who’s moving.
— Matt McManus
Co-founder, Gents Journey
The Only Way Out Is Through
👊 THE MOVES
Media for men.
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Make Fear Your Friend
Treat fear like a compass; it points you toward what you care about most.
If it scares you, it has meaning, and that’s all the more reason to push through.
Watch Fear: Go Towards It.
Typically, the day-to-day fear we experience is simply a story we’re telling ourselves.
Here’s a good acronym to remember F.E.A.R.:
F: False
E: Evidence
A: Appearing
R: Real
Back in the day, cavemen had real fears, such as whether they’d eat, be eaten, or survive the elements.
However, today in the age of technology, push notifications and constant emails, we remain consumed by the expectations of others.
We worry about what others might think of us, or what we “should” or “should not” do.
A mentor of mine once said, “Wipe the should off of you.”
Gary Vee or Bust
When Gary Vee released his limited-edition K-Swiss shoes, he came to Los Angeles, where I was living at the time, for a meet-and-greet to sign his kicks.
When I got there, the line stretched down Melrose and wrapped around the corner.
Previously, a mutual friend connected me to Gary, which led to me applying to work at VaynerMedia. I was asked to stop by and say hello, and felt this would help my chances of being hired.
I saw the line of 500+ people and said to myself, “This is it, I have to do this.”
It was time to uphold my commitment to his company and myself.
A doorman stood at the entrance, letting attendees in one by one, as I could see the entrance at the end of the block.
I started walking past everyone in the line, nodding and pushing forward.
What will they say? my inner critic asked. Even though I was scared, I ignored it and kept on.
What if the doorman stops me? I listened and kept moving forward, one step at a time.
What if this doesn’t work? I acknowledged the fear rising within me, thanked it, and said to myself, “Why not me?”
As Wayne Gretzky said, “You miss 100% of the shots you don’t take.”
I held my head high, walked with intention, grabbed the door handle myself, and walked right in, as I nodded to the doorman.
“I am meant to be here,” I told myself.
I entered the queue inside, introduced myself to the K-Swiss team, got their business card, and then stepped up to take a picture with Gary.
Needless to say, I didn’t get the job, but I came away from that with much more.
It was a lesson in commitment, and if you want something bad enough, it’s up to you to go get it, even if you’re scared.
Or as my friends say, risk it for the biscuit.
Take the First Step
What are you afraid of?
Maybe it’s asking out the girl, starting a hobby, or quitting your day job for the dream career you’ve always wanted …
You are a man of courage, confidence, and bravery who owes it to himself to try.
Start noticing when your chest tightens, or your heart won’t stop racing. Write it down on your phone as you build a sense of awareness of what is impacting your life.
These are the moments to recognize the voice in your head and say, “Thank you for pointing me in the right direction.”
Fight or flight is real, and your job is not to run or resist, but to move forward in the face of fear and adversity.
Try this: Pick one thing that feels hard, or that brings up fear in you, this week.
One caveat: keep it within reason. Don’t start fighting bears or jumping from buildings, unless you know what you’re doing and aren’t putting your life in danger.
For Example: Make sure to get in shape and train first, before trying parkour.
Every athlete started somewhere, with one step, one jump, and one leap of faith.
Start small, but do it scared. Make fear your friend.
Comment below with one time you took a leap in the face of fear, and how it landed.
— Stephen Seidel
Co-founder, Gents Journey
🔗 MEANINGFUL MENTIONS + MAGIC LINKS
Fun stuff you’ll dig about our theme of the week.
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✨ PREMIUM MEMBERS ONLY
Until next week,
—The Gents
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