What’s the opposite of a winner?

Not a loser.

The opposite of a winner is someone who doesn’t know that they’re capable of being a winner.

You could finish last, and still learn something valuable. Or you could finish last, and quit because the skill ceiling is too high. It doesn’t matter if the game is too hard. It doesn’t matter if the grammar is too complex. What you measure is your reward.

You could cheat your way to first place, and become a better cheater. You could fail your Japanese class, but still know the difference between “に” and “に.” In both cases, you’re a winner: you’re still gaining something.

The question is: what are you trying to win?

A few tips from Day Zero of Performative Speaking

Lighting. Clothing. The speed of your voice. Are you looking at the camera, or looking down at the ground? Sit up straight, but don’t stiffen up like a skeleton. Is there anything distracting in the background?

These details matter. You might have groundbreaking ideas, but it doesn’t matter if you can’t convince anyone to put their phone in their pocket while you speak.

Performative Speaking is only just beginning. I’ve already learned much from Robbie Crabtree about why good presentation matters as much as having good stories.

The Penguin Latte Podcast #17 – Marketing as Self-Expression with Arielle Kimbarovsky

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Are advertisers evil? Are marketers the scourge of the earth, hell-bent on stealing our attention and selling it off to some nameless corporation? Yes, and no. It’s every good marketer’s job to capture our attention. And advertisers get paid to understand what makes people want to buy things. But to call either evil would be like accusing your grandma of being a Satanist (unless she really is one). The best marketers get us as excited about products and services as grandma makes us excited about fresh chocolate chip cookies.

In this episode, I speak with one of the most delightful and creative marketers I’ve ever met: Arielle Kimbarovsky (@ariellekimbar on Twitter). Arielle Kimbarovsky is the head of social media and marketing for M1 Finance. Her spec work portfolio (got it right that time) is full of an exuberance that reveals her eye for color choice, words that evoke powerful emotions, and stories impossible to forget.

If you’ve listened to my episode with Robbie Crabtree, then you know how much I value communication. Design is a form of communication. Some of the most difficult problems I’ve had with the blog and podcast were to pick the right words, color choice, shape, and names for titles. What you say matters less than how you say it. This episode serves as an opportunity to learn how to express yourself through multiple mediums: painting, writing, talking, music, video— nearly all the topics we discuss relate to communication. We also discuss reading, being introverted, taking breaks, being yourself, and thinking big. It’s a wide-ranging conversation full of possibility and delight.

So, please enjoy my conversation with Arielle Kimbarovsky!

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This episode is brought to you by my weekly newsletter, Hey Penguin. Hey Penguin includes tips for improving yourself through creativity, plus a bunch of extra goodies like drafts of blog posts, art I’m digging, letters from my audience, and previews of podcast episodes. Sounds good? Click here to subscribe and get the next issue delivered straight to your inbox.

PS: Does The Penguin Latte Podcast remind you of the excitement of fresh presents on Christmas morning? If so, please consider leaving a review on Apple Podcasts/Itunes. It takes all of 60 seconds (or 120 seconds if you’re feeling extra spicy). By leaving a review, you’re making the podcast 1% better. So, if 500 of you leave reviews, the podcast gets 500% better (if I have my math right). Plus, I love reading all of your juicy comments.

Thanks so much!

The highest benchmark for every creator

Two friends asked me if content creators should have separate channels. One channel for business content (whatever that means). Another for personal content.

If you think your personal life is more interesting than your job (content creation is a job), yes.

And if that’s true, then you must know that you’re boring yourself and your audience with your content. Listen to the voice that’s begging you to do something totally off the cuff. Don’t make your audience navigate extra links. Deliver the goods up front.

If your job is to tell good stories, no. All good content creators know this. Their job is to tell good stories. Their job is to express themselves through stories about people, places, products, and ideas.

Not everything personal needs to be about you. John Daub makes personal YouTube videos even though he rarely talks about himself. John Daub loves Japan, and so he makes videos about Japan. He doesn’t have a separate channel about his life. Japan is his life.

The highest benchmark for every creator isn’t a million subscribers or followers. No, the highest benchmark is a story you never get tired of telling.

“If you can tell a good story, you will always have a job”

John Daub

PS: A job should be challenging, rewarding, and something you’re proud of. I spoke with John Daub a few weeks ago about what it means to have a job that hits all 3 of those qualities. It’s one of the shorter episodes of the podcast, but one of the most beautiful conversations I’ve ever had. I hope you’ll have a listen. It’s magical.

Everyone gets a Sunday

In some cultures, Sunday is the beginning of the week. The foundation of the day, grounded in rest and recovery.

No matter what culture you’re a part of, you’re guaranteed one Sunday a week. Of course, not everyone gets to dedicate a whole day to resting. You might be the busy mom who uses Sunday to prep for your kid’s meal plan for the week. Or you might be the busy teacher grading all your student’s midterms.

If you can’t find your rest on Sunday, I hope you can find some pockets of rest throughout the week. You deserve it.

The Penguin Latte Podcast #16 – The Wizard of Speech: Robbie Crabtree on Mastering The Spoken Word

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“Virtually everything you do, on a day to day basis, is public speaking.”

Communication is everything. The way you speak to yourself and the way you speak to other people is as important as breathing. Your words can either help you get to where you want to go, or they can lead you to a place full of misery and regret. I’ll remind you again because it’s so important. And I’ll even bold and italicize the word for your convenience.

Communication. Is. Everything.

Today I’m excited as all hell to be joined by a master of communication: Robbie Crabtree (@RobbieCrab on Twitter, personal website here). Robbie Crabtree is a trial lawyer with over 9 years of experience handling some absolutely devastating trials. Domestic violence, murder, child abuse, whatever horrible aspect of the human condition you can imagine, Robbie has dealt with it.

At the heart of Robbie’s work is the art of storytelling. Robbie knows how to craft an interesting story out of anything. And I seriously mean anything. He can make a story about your bar mitzvah as exciting as a day at Six Flags.

Robbie Crabtree is also condensing his 9 years of speaking experience into a premium online course called Performative Speaking. Performative Speaking teaches people how to speak in a way that’ll keep any audience on the edge of their seat no matter what you’re talking about (even bar mitzvahs). I can’t imagine a better person than Robbie to put on a course about public speaking.

The Keys to The Universe

This is very *meta* episode. Listening to Robbie speak made me a better podcaster. But even if you’re not a podcaster, YouTuber, or don’t believe that your job has anything to do with public speaking, make no mistake: the world is paying attention to the way you communicate with it. There’s no such thing as a job that doesn’t require effective communication.

There’s gems buried in this episode that might not be apparent the first time around. For example, why did Robbie talk about Yu-Gi-Oh, of all things, in one of the most emotionally difficult trials of his career? Why did Robbie ask me what time it is (even though he knew the answer) halfway through the episode? What is it about Jack Butcher that makes him such an effective communicator, while using so few words? And what’s the key distinction between public speaking and giving a speech?

You’ll have to listen to find out.

Listen on Spotify | Listen on Apple | Watch on YouTube


This episode is brought to you by my weekly newsletter, Hey Penguin. Hey Penguin includes tips for improving yourself through creativity, plus a bunch of extra goodies like drafts of blog posts, art I’m digging, letters from my audience, and previews of podcast episodes. Sounds good? Click here to subscribe and get the next issue delivered straight to your inbox.

Some fundamentals of personal branding

I used to believe that personal branding is personal.

It’s not.

Personal branding is tailored. It’s tailored to the subjective experience of whoever engages with your work.

Everyone perceives the world in their own way. And your audience experiences your work in their own way, as well.

Alice reads a blog on productivity because she wants to learn how to get more work done. But Joshua reads the same blog as Alice because he’s a productivity fiend. Not only is Joshua looking for ways to be more productive, he’s seeking the hottest productivity tricks to share with his friends. Same product, different experience.

Personal branding isn’t exclusive to the entrepreneur, or the YouTube star. Personal branding is the feeling you get after eating your favorite meal. It’s not about the actual work while it’s happening to or around you. Because that’s when you’re actually in the thick of it, and you’re not aware that there’s magic happening. But afterwards? After you’ve complimented the chef? After you’ve left an unusually generous tip? That’s when you know you’ve experienced something remarkable.

And as an artist, or an academic, or a well-groomed professional, you have a personal brand. You have a stamp. You have a footprint to leave behind. “This is the work I’ve done for you. I’m proud enough of this work to put my name on it.”

You can do personal branding even if you don’t leave your name on it. Consider the work of an anonymous Japanese chef. Anyone who eats this chef’s curry udon, without knowing the chef’s name, knows who cooked it. The branding is in the hard-work of delighting the customers after they’ve finished their meal.

Do you think about an actor’s performance after the credits roll? That’s personal branding.

Do you think about the taste of the first sip of your morning coffee, when there’s no more coffee left? That’s personal branding.

Personal branding is how your readers think about your blog while they’re daydreaming.

It’s how your audience geeks out about your work behind your back.

It’s how they’re spreading messages (good or bad) about your work through social media and emails.

But you don’t “create” a personal brand. When you lean into yourself, you create a body of work which becomes an obsession for your fans. This is why artists sometimes respond with, “I don’t know, it just sort of happened” when asked how they got the ideas for their best work.

No great works of art are made by force. They “just sort of happen.”

Your true fans are those who obsess over the work that “just sort of happened.” And when you have thousands of those kinds of fans, that’s when you know you’re good at personal branding.


Personal branding is about showing up, uncensored, unfiltered. But that isn’t the same as offensive or rude. It’s about adopting the mindset of the professional who doesn’t take themselves too seriously.

If you’re dealing with impostor syndrome, or self-doubt, please consider scheduling a chat with me. I’d love to help you get unstuck so you can make work you’re proud of, and share it with folks who care.

Help I’m being engaged at!

The comments section is the most under-leveraged asset.

It’s not a place to test out your new emoji keyboard.

It’s a place to say, “hey I really like what you said. Let’s take this even further.”

Did someone take time out of their day to write a comment that’s more than three words long? Return the favor.

The comments section is not a place to shortchange empathy, either. The problem isn’t “thanks for this, I needed that.” That’s fine. You said exactly what you wanted to say. The problem is, “if I respond to this, how many more followers will I get?”

Every time I write an essay as a response to a comment, I’m surprised at how surprised people get. It’s sad, actually. How many people are crying out for someone to hear, see, and work to understand? To have someone say, “I sort of get what you’re saying, but could you go further?”

The stereotype of the desperate salesperson has been replaced by the value hound. Sub-for-sub. Free subscribers. You follow me, I follow you. Oh, I see. You’re trying to engage at me, rather than with me.

Being engaged with. That’s what delights us, surprises us, makes us miss you when you’re gone.

Seen, heard, understood.

Eye contact.

How to develop better judgment without knowing everything

Judgement is the skill of considering what’s relevant before making a decision. Relevant includes the known and unknown. How the customer could react matters as much as how they’ve been reacting.

Let’s say that you’ve conditioned a customer to trust you by delivering on your promises.

That’s the known.

But today, a new problem is frustrating the customer.

That’s the unknown.

Now your job to show the customer that they can still trust you, even with problems like this. Because this customer doesn’t know (yet) that they can trust you when it seems like a problem has no solution.

Judgement is about more than the Big Business decisions.

Judgement means giving this podcast guest extra time to think about the question.

Or letting this person speak without interrupting them.

Or empathizing with this client’s particular (and maybe annoying) needs.

Or understanding how to operate on this person’s overcrowded mouth.

How to develop better judgement?

Not by attending a seminar. Not by signing up for a class.

You develop better judgement first by accepting that you cannot know everything. Sending these firefighters into a burning building could cause something terrible. But the good captain is aware of the risks, and proceeds anyway.

And the 911 operator doesn’t ask the caller to backtrack. “Sorry, we can’t put out the fire because you’re not giving us every fact about your situation. Goodbye.”

Developed judgement comes through gained experience. Gained experience comes from exposure to all the relevant situations. And the only way to gain the experience necessary for making better judgments is to never settle for familiarity.

If you’re having a first consultation with a dentist, and they’re already familiar with the inside of your mouth, then I recommend you install a new home security system.

How to tell who has good judgment?

Seek out those who seem to be playing the archetypal fool. Seek out those who say, “I’m not sure.”

“I’m not sure” doesn’t mean “I’m not interested.”

If you stop listening after “I’m not sure,” then you’ll never hear the second half: “so I need to figure this out.”