The Penguin Latte Podcast #21 – Jamie Russo: Entrepreneurship for Positive Change and How to Spread A Million Acts of Kindness

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Warning: my guest today is a very, very kind person.

Today on the podcast I’m talking with Jamie Russo (@jamierusso), creator and writer of the Goodnote newsletter. I love Goodnote! And to think of it only as a newsletter would be a mistake. Goodnote is a proxy for Jamie’s quest to spread 1 million random acts of kindness. He’s using his writing platform as a means to an extraordinarily compassionate end. Check out these little blue postcards he mailed me. If you’d like one, reach out to Jamie on Twitter by clicking here.

We talk writing (as I usually do with my guests), volunteering, why Jamie cares so much about people, working with compassionate companies, helping people at scale, the benefits of walking, how to use entrepreneurship as a force for positive change, how to find your guiding force in life, and much, much more.

I had so much fun talking with Jamie, and at the end of our talk my cheeks were sore from smiling so much. You won’t want to miss this one. Please enjoy!

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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 on Sunday.

The Penguin Latte Podcast #12: Shelby Smith on Lessons From Failures, Language Learning, and Having the Courage to Get What You Want

Today I’m joined by the bold and adventurous Shelby Smith.

Shelby Smith (@CoShelbySmith) is head of user onboarding for LingQ. She’s also a writer who discusses leadership, language learning, self-development, and why it it’s important to stand up for yourself to get what you want.

Listen on Spotify | Apple Podcasts | Watch on YouTube

Talking Points

  • Shelby’s backstory with the entrepreneurial spirit (2:30)
  • “I’m a day one listener of The Tim Ferriss Show” (6:00)
  • Action is the missing ingredient / Life in Ecuador (9:00)
  • Learning from having a failed business (15:00)
  • “I wrote that I was psychic” / How to handle job interviews if you never went to college (18:00)
  • Suggesting what companies do wrong (35:00)
  • What it was like to go for a year without social media, and all the unexpected changes that came from doing that [I can’t believe this is even a talking point] (41:00)
  • “Build a personal relationship with your ideas” / Experience with Write of Passage (1:00:00)
  • Shelby’s guiding principles (1:07:00)
  • On learning languages (1:15:00)
  • How we elicit meaning in language (1:25:00)
  • What’s the work you do that feels like play? (1:30:00)
  • When was the last time you were in flow? (1:35:00)
  • When do you feel dissatisfied? (1:38:00)
  • The final question (1:42:00)


The Four Hour Workweek

The Art of Learning

Deep Work


Discipline Equals Freedom


Tim Ferriss

Jocko Willink

Josh Waitzkin

Samuel Hulick

Cal Newport

Ray Dalio

Richard Turner




The work of a creative professional starts with a signature

What does a creative professional do, exactly?

Do they show up to a marketing firm with a bunch of coloring books and crayons?

Do they throw paint everywhere and make a bunch of abstract art and then try to sell it to advertising agencies?

Do they run B2B slam poetry gatherings over Zoom?

That stuff is cool, but the creative professional likes to get paid.

So what do they do to get paid?

They look at your organization’s copywriting, marketing assets, leftover zoom videos, blog posts and articles, and they make something useful. The creative professional takes a bunch of disparate stuff, stuff that sort of has a coherent message, and they find the signal in the noise.

The creative professional connects the dots using their signature.

Mark Woollen & Associates, the team behind my favorite movie trailer, has a signature. I get goosebumps every time I watch their brilliant piece for The Social Network.

The late Toonami had a signature. Their nighttime commercials on Cartoon Network created a generation of lifelong fans. For the Toonami faithful, exciting commercials are synonymous with the (sadly, now defunct) Toonami brand.

If you’re lucky, you’ll find your signature right away. But if you’re like all the others, it’ll take you a very long time to find it.

So what’s the payoff of spending months, maybe years, looking for your signature?

Liberation. You’ll no longer be oppressed by the temptation of the cliched and popular. You’ll start writing about your weekly hiking trips. You’ll start recording podcasts about black coffee and flannel hoodies. You’ll no longer bore yourself with what you make. And the people who work with you won’t be bored, either.

It’s the creative professional’s job to rid the world of boring stuff. And the only way to do that is to start developing a signature. If you don’t, you’ll end up making stuff that’s like all the other stuff out there.

Your signature is a currency that increases in value the more you spend it. The more you use your signature, the better you’ll be at using it. A stronger signature will lead you to bigger and better projects. Bigger and better projects means bigger and better pay, which leads to more opportunities…you can see where this is going.

And sure, people can counterfeit your signature. But like a fake dollar bill, the forgery will be obvious once you hold it under the light.

The point of creativity is to solve problems in interesting ways. The creative professional gets to show up, armed with a pen in hand, prepared to do something that might blow up in their face. But the risk isn’t as big as it seems. There’s always a silver lining in every failed project.

For the creative professional, the world is like a giant contract. They go out and sign their name here, here, and here.

Gifts with no wrapping paper

Jab, Jab, Jab, Right Hook is Gary Vaynerchuk’s best book.

Here’s the whole book in a sentence. Give more than you ask.

Pair that with Essentialism by Greg McKeown. In a sentence: stop doing things that aren’t helping you do what’s important to you.

Combine those two ideas, and you get this: use only the tools, platforms, and mediums that work with the gifts you want to share.

Consider Dr. Jordan Peterson’s lectures. His popular rule, “Compare yourself to who you were yesterday, not to who someone else is today” is short enough to be a tweet. But that wouldn’t be as valuable and entertaining as his lengthy yet cohesive explanation of the idea.

Dr. Peterson didn’t come out first by saying, “I’m a clinical psychologist. Here’s what I know. If you want to know more, here’s what you’ll need to pay me.” Instead, he put all his lectures on YouTube so that anyone could watch them for free. This is why Peterson is now a household name (in houses with clean rooms).

Know which tools work best with your gifts. Give your gifts. And then ask people for something in return. If you ask before you give, you’re giving them a reason to ignore you.

Nobody is “gifted.” But everyone has gifts. You know things that I don’t – until you teach me what you know. You’ve experienced things that I’ll never experience – until you share those experiences with me.

What are your gifts? Your gifts are the things you know, the feelings you want to spread, the changes you want to make.

You already have a wheel. No need to reinvent it.

What to do if you don’t have “three years of experience”

I know I’m late in saying this, but the Internet is 4w3s0m3s4uc3. I’m getting help for my new consulting service from an experienced consultant in Australia. A generous young teacher from India improved my resume. And I had a two hour conversation with an artist from Wichita.

For many, it seems like the biggest barrier to doing good work is “three years of experience required.” But we can work around that.


By seeking people who have the experience. By being curious enough to ask them the right questions. And by being so enthusiastic about the work it’s almost overwhelming.

It doesn’t help to start by asking, “what should I do with my life?” because you “sort of” know the answer already. By asking someone what to do with your life, you’re seeking permission to do what you’ve always wanted to do.

Instead, try, “I really like what you’re doing. I want to do the same. But I’m not sure how to go about doing this.”

And how should you express your enthusiasm without stepping over boundaries? It’s like I said before. Ask the right questions.

If you don’t have “three years of experience” yet, enthusiasm and curiosity are your greatest assets.

For our amusement

Why should we make anything at all?

For our amusement.

And if we’re making things for our amusement, does that mean we shouldn’t share anything we make?

Of course not. Experiencing art we enjoy is like looking at a mirror. And as creators, we’re making mirrors for people to look at and see something we can’t see.

Some of us look at the mirror and notice technical finesse (or error). Some of us look and see emotions we can’t put into words. And some of us hear the subtle tempo changes.

The artist knows more about their art than the audience does. That is, until the artist shares their work. It’d be overwhelming for the artist to know all the ways the audience might experience the art.

When your work is out there, it’s out there. It’s impossible to control how the audience appreciates your art. To be upset that your art wasn’t well received is to be the mother who’s upset their kid didn’t want to live the way mother wanted them to.

Where does self-worth come from?

It’s sad we’re even asking this question.

We find the answer when we first ask, what are we?

Well, I know what we’re not. We’re not a collection of numbers.

We like to focus on growing our metrics. Get more subscribers. Get more followers than we had last Thursday. But the numbers don’t define us. The numbers are something that somebody else invented. And we’re not defined by something that exists outside ourselves. So we shouldn’t tie our self-worth to something external. Because what exists outside ourselves could be taken away from us.

Put some distance between you and what you see. Who you are isn’t what you see. You’re not your social media numbers. You’re not the number of people retweeting your latest bit of wisdom.

What’s dangerous about tying our self-worth to numbers is that a number can always be higher. And it can always be lower, too, which is why we prefer them to be higher. Lower numbers means we’re less significant. Higher numbers means we’re accepted.

You’re a collection of experiences. But, like the numbers, you don’t have much control over your experiences, either. You couldn’t have asked your mother for an abortion.

But what you always have is control over your perception. You can choose how you’ll perceive the fact that you were born.

We lose our wallet in the same place we lose our self-worth. “Oh, it’s right in front of me.”

What’s in front of us is what blinds us. What we see always hides something else.

If you’re seeing numbers all day, then you’ll unconsciously tie your self-worth to the numbers. What gets measured gets managed, right? What gets measured gets managed by our ego. It’s our ego’s job to tie our self-worth to what we’re seeing on a day to day basis.

This is why it’s healthy to disconnect and go for a walk. Put nature in front of you, and you’ll soon realize how expedient the numbers are.

Solve or signal?

Are we building to signal how many bricks we’ve laid?

Or are we building because we see a problem that needs solving?

Measurements are necessary, of course. The architect needs to know the proper amount of all the materials and the cost of each.

But we always have the option of turning measurements into signals of our influence.

A friend of mine pointed out that we shake our heads at anyone who flaunts their income. But when we see people we like signaling how much they’ve earned off of their products, we let it slide. We become enablers of the behaviors we shake our heads at. Because they’re doing it “holistically.” They’re sharing their secrets to success in under 280 characters. To us, we feel like we’re part of their journey. Because if they can build something with only a few viral messages, so can we, right?

As creatives, as builders of remarkable things, we have a choice: solve or signal?

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.

This might sound stupid, but

it’s not.

Let yourself say the stupid thing. As long as you’re not being offensive for the sake of being offensive, you’re fine.

I flinch when I hear myself editing my words out loud. This happens either before or after I speak. Sometimes both. “This might sound stupid, but…” or, “that sounded so…”

But when I watch myself being authentically stupid, without hesitation or self-editing, that’s when I start smiling. I’m not smiling because I enjoy hearing myself saying stupid things. I’m smiling because I wasn’t holding back. I was fully present in my stupidity.

Authenticity doesn’t mean that you shouldn’t apologize for saying something unwarranted. Authenticity means no hesitation, no editing.

When you’re editing live in front of somebody, you’re no longer present in the conversation. You’re in the future when you start with “this might sound…” and you’re in the past when you say “that sounded so…” But you’re in the present when you say the stupid thing. There is no ego in the present. Only your stupid Self.

Speaking mode, listening mode, writing mode. All for the present.

Be here now, be authentic, be stupid.