Unconventional Insights For Confident Speaking

Dear Legend,

I’m writing this letter to you at 5am after my morning workout. As I was on my bike this morning (most of my ideas come when I’m biking or running), I realized that there is something I have to tell you in this issue of Legend Letters.

It’s about an epiphany I had last week! (About how to make tough decisions). And I can’t wait to tell you all about it. But I’ll have to leave it to the later part of this letter. I first need to share something else with you:

An interview I had that has the power to change your life.

It’s not hyperbole. It truly CAN change your life (I mean it).

That lesson?

How to speak with confidence.

How can speaking confidently change your life? You already know this, but I’m going to tell you anyway.

If you can speak confidently, you can get attention. If you can get attention, you can shape beliefs and change minds. If you can change minds, you can influence a new behavior and if you can do that… you can make anything happen.

But just like you, most people know this, and they would still rather be in the coffin than give the eulogy. According to a published research study, 77% of people fear public speaking more than death (there is even a name for this: glossophobia - crazy!)

What happens?

Some freeze. Some stutter. Some get the shakes so bad they could mix a martini in their hands. And it’s not because they lack intelligence or expertise—it’s because speaking triggers something primal, something deep in the human brain (I’ll share more on this later).

And people have been giving advice to speak better for centuries. Most of them suck. Have you heard of advice like this?

“Just be confident”

“Get in a power pose”

“Picture the audience naked”

I don’t know about you, but they don’t work for me. So what did I do? I found a speaking coach to interview. Not just any speaking coach, this person has spoken at 1,000 plus events and interviews, helped more than 300 executives and CEOs, been on 3 TEDx stages and has trained leaders at Amazon, SAP, and IBM.

Her name is Nausheen Chen and it seems like she knows what she’s doing!

Because of all the BS advice that’s floating around out there, I wanted to see if she has a different take. It turns out she absolutely does.

I uncovered four unconventional lessons from Nausheen to help you get better at speaking or at least spur you to invest in your speaking skills (watch your life change once you start speaking and sharing your ideas!)

Ready?

Here we go.

One—Fake it till you make it is a lie.

People tell you to just act confident. That’s the most ridiculous and unhelpful thing to say, because what if you just don’t feel confident? What if you’re dying inside while you’re up there on stage pretending to be some smooth-talking, polished presenter?

Nausheen herself went through this. “I could command a room, but inside, I still felt like an imposter,” she said. “I had trained myself to act confident—but I never built the internal confidence to back it up.”

Turns out, confidence has two parts: outer (posture, tone, gesture) and inner (believing that your message deserves to be heard).

The problem is that most people work on outer confidence, not inner confidence. So what should we do?

Stop chasing external validation. Instead of asking, “How did I do?”, ask, “Did I say what I needed to say?”.

Decide—right this second—that you deserve to speak. (Your purpose is meaningful and your message deserves to be heard)

So how do we combat the shakes? 👇🏽

Two—Your brain thinks public speaking equals death, time to retrain it

Have you ever wondered why your heart races before a speech?

Why your hands shake? Why you feel like you might actually throw up?

Blame your caveman/ cavewoman brain.

“When you stand alone in front of a crowd, your brain perceives this as a literal threat,” Nausheen explains. “For early humans, being separated from the tribe meant you were vulnerable. And vulnerability meant danger.”

That’s why public speaking feels like life or death.

But you and I know the truth, right? I know you do…

Speaking in front of people won’t actually get you eaten by a saber-tooth tiger. It won’t get you banished from the tribe. (In fact, it might even increase your status in the tribe.)

So how do you retrain your brain? Three things:

1. Breathe: Inhale for 4 seconds, hold for 4, exhale for 6. It tells your nervous system to chill

2. Move: If you stand stiff as a board, your brain thinks you’re “trapped.” Movement = confidence.

3. Reframe: Your body doesn’t know the difference between fear and excitement. So tell yourself: I’m not nervous. I’m excited. (This was such a game changer for me when I was on a stage a few weeks ago in front of ~100 people.)

Ok, I might need to come back to writing this letter. I hear some screaming upstairs.. I think my 4 year old is up. Hold on…

…

I’m back. She just had a bad dream, and just needed some snuggles to get back to bed (times like these I tell myself “I get to have these moments” and it just makes everything so much better).

Onward.

Three—The reason why you’re truly afraid to speak (it’s not the audience)

Here’s the truth.

You’re not afraid of speaking. You’re afraid of being judged.

Most people don’t stay quiet because they lack the skill or the ideas, they stay quiet because they fear judgement. Do you agree? I know you do.

• What if my coworkers think I’m full of myself?

• What if my friends roll their eyes at me?

• What if I mess up and look stupid?

And guess what, it’s not just lay people like us, it’s CEOs, founders, and executives too. Nausheen worked with many of them who were terrified and it wasn’t because of the strangers in the room, it’s the people they knew.

Nausheen shared this quote that changed my perspective forever:

“Most people aren’t afraid of speaking—they’re afraid of being seen,” she says. “But if you never let yourself be seen, how will the right people ever find you?”

Read that again.

Give people the chance to find you, to be served by you.

Your biggest critics are never doing better than you. The ones judging you? The ones who “don’t get it”? They aren’t stepping up, they are hiding in the shadows. And the real truth? They are probably not even thinking or judging you in the first place! (That’s the spotlight effect)

So why let them hold you back?

Here’s what to do:

• Speak to the people who need you. (Ignore the ones who don’t.)

• Let them judge. (It’s not your problem.)

• Start small, but start now. (Speak up in a meeting. Post something. The fear fades when you do the thing.)

But you’re not born with the gift of gab…what do you do?

Four—Great speakers aren’t born (they’re made)

Public speaking is not an innate talent. It’s a trainable skill.

Sure, some people might have some natural talent, but the best in the industry? They got there through practice and hard work.

Nausheen has coached billion-dollar CEOs who run companies effortlessly but freeze on camera. Why? They never trained for it.

“Speaking is like dancing,” she says. “You might feel awkward at first, but with the right technique and practice, it becomes second nature.”

So instead of blaming the speaking gods of not giving you the natural gifts of public speaking, here’s what to focus on instead:

• Content clarity – Speak in stories, not data dumps.

• Outer confidence – Open posture, strong eye contact, controlled pace.

• Delivery skills – Master your voice, energy, and body language.

The secret? Repetition.

No one gets good overnight. But the people who look “natural”? They’ve just done it more times than you.

So…

what do you think? Will you take the mic?

Think about how your world will change if you speak up more.

The world listens and bends to those who speak up.

• Want to be seen as a leader? Speak up

• Want to serve more people? Speak up

• Want to inspire your community? Speak up

And so on… I’m going ask you again, will you take the mic?

I sure hope you do, because that’s one of the best ways to make your mark and live your legend—sharing your ideas by speaking up!

(If you want to listen to the podcast episode where Nausheen and I dive deep into the intricacies of speaking and communication, listen on Apple, Spotify or on the web.)

Now…

I haven’t forgotten about that epiphany I was going tell you about. Have you? Maybe so, but now you remember.

I had better hurry though, it’s almost 7am and I need to head upstairs and start getting breakfast ready for the fam!

The question: how should you make tough decisions? 

I was pondering this because I had a tough decision to make. I had an idea to gather up almost 20 years of experience and package it into a program. But like anything in life, I need to think about opportunity cost. Which means if I take this on, what am I giving up? Should I do it?

I tossed and turned, I talked to many people about this idea and the feedback was 50/50. Some folks told me to go for it, while others told me to focus. I started to list out pros and cons, think about different scenarios and it was driving me crazy.

The epiphany…

Instead of asking all these questions and banging my head on the wall. There is really only ONE question that is meaningful:

Will you regret NOT doing this?

And the answer was “I will definitely regret it if I didn’t do it”. And that was it. There is actually a name for this framework - it’s called the regret minimization framework (watch a short video where Jeff Bezos shared it years ago). It’s going to be my goto question whenever I have a tough decision to make.

I never mentioned what is program even is did I? Silly me. It’s called Medtech Brand Academy, designed for medtech marketers to level up their brand strategy game.

Ok, I really need to run very soon… if not I’ll have two hangry monsters running around!

But before I do, today’s #PSYCH! effect is…

The Peak-End Rule.

The key thing to remember about the peak-end rule is that people have bad memories.

We don’t remember entire events, we mostly remember two things:

• The most intense moment (peak)

• How it ended (end)

It’s why a so-so meal feels amazing if they surprise you with a free dessert. Or why a long procedure with a gentler ending feels less painful than a shorter but more consistent one (Study here).

So what does this mean for you?

Make your best point the most intense and end on a high note. 

(Mic-drop moment. Surprise bonus. Something that sticks.)

People forget the middle. They always remember the ending.

Alright, I really gotta run! I think it’s going to be french toast today, let’s see if we have some brioche bread in the pantry.

I hope this letter ended on a HIGH note for you!

I’ll see you next Sunday.

Make your mark, live your legend 🤘🏽,

Howie Chan

Creator of Legend Letters

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P.S. I hope you enjoyed the new format - email me, let me know! 🙏🏽

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