My Inner Circle of Evil: How Bad Influences Help You Succeed

Have you ever shared a project with a friend or family member, hoping to get some feedback?

This is great!

Wow, I love this

Your father and I are so proud of you sweetheart

This is great I guess this explains why you never return my calls

This isn’t feedback. It’s protection.

Feedback hurts. We’re programmed to avoid getting hurt. And so we avoid feedback.

The most promiscuous way we avoid feedback is surrounding ourselves, for our entire lives, with a circle of friends and family members that “only have our best interest at heart” (read: I want to suffocate you with a pillow.)

Make friends with people who have skin in the arena. Make friends who know which game you’re playing, and know the rules like the back of their hand. Make friends who understand that not taking risks is the riskiest risk of all. Make evil friends. Dastardly friends. Viscous friends, friends who might hurt you!

…with feedback.

My inner circle of evil is a group of 6* people I can rely on for feedback. Real feedback. The feedback I’d rather not hear, but need to. I don’t bother them with drafts of these daily posts. I send the big guns. The risky stuff. The projects with a high probability of failure, the stuff that people might mock me for. These friends are a bad influence on me. Their insidious charisma seduces me into doing things I don’t want to do. They tell me to aim higher. They tell me to raise my hourly rate. They tell me to start a business. They tell me to “fuck it.”

And fuck it I do.

Who’s in your inner circle of evil?

*The most evil of numbers

Rockets: A Year of Posts

If you hear a voice within you say ‘you cannot paint,’ then by all means paint and that voice will be silenced.

Van Gogh

Tomorrow marks the one year anniversary of my daily blog. I knew I’d make it this far, but I didn’t think I’d come out alive.

But I’m still alive. I’m still writing.
And I’m only a little less terrified of showing up to serve you.

Writing a blog a day is the best decision that I make. It is the most spooky, gut-churning, I Want My Mommy thing that I do. I Want My Mommy because it’s a commitment. And commitments offer no place to hide.

There’s a billion blogs, but very few commitments.

We can take that statement and apply it to any medium.

A billion podcasts. Few commitments.

A billion newsletters. Few commitments.

A billion books. A billion workshops. A billion Chrome extensions.

The world does not lack good ideas. Everyone has at least one or two good ideas. Everyone has ideas that would launch them into a new life, a life bigger and better than any life imaginable — ideas that would launch them to the moon!

Ideas are like rocket fuel. But you can’t send a rocket to the moon without a launchpad. And you certainly can’t launch a rocket to the moon without brave, responsible individuals willing to take a risk, willing to bear criticism, willing to fall flat on their face.

Choosing to write in public everyday means choosing to fall flat on your face. Again and again.

But eventually, you will get used to the bruises.

If you’re new here, here’s some posts that people seem to like.

Making stuff is easy.

I’m setting the bar really, really low this year.

Everything I know: Sacred Tips for The Restless and Creative

Shitting my Pants: Why Self-Criticism Is My Closest Ally

To be your toughest critic is to be your closest friend

Lazy critics ignore the significance of the work they’re criticizing.

Good critics, especially harsh critics, crave improvement.

If you’re a lazy self-critic, you won’t appreciate the amount of work required to achieve your goals. You will pounce forward, collapse before the finish line, and blame the loss on yourself.

The lazy self-critic doesn’t respect the difficulty of the goal. Unlike the tough self-critic – the self-critic who craves improvement – you’ll frame your incompetence as static. And maybe it is. Maybe you’re not cut out for the big leagues. Maybe this is a waste of effort. Maybe slamming your head against a wall isn’t the best way forward.

If you’re a tough self-critic, you realize the mismatch between your goal and your incompetence. If you’re a tough, reasonably harsh self-critic, you’re okay with never being comfortable in your own skin.

Constantly bothered, motivated by their incompetence, the tough self-critic sees the day as another shot at success. But the journey doesn’t end at the finish line, at the trophy ceremony, at the pop of the champagne bottle. Nor does the journey begin again when success is finally reached. For the tough self-critic, the journey – the great journey – is the process of constantly striving to be their best in any situation, no matter how ugly, disagreeable, or stressing.

Do yourself a favor and criticize yourself. You’ll be glad you did. I do it all the time. I think everything I make is shit. Really. Everything. On my worst days, I think everything I make is as embarrassing, foul and retched as shitting my pants with no restroom in sight. When I feel more forgiving, everything I make is as good as leftovers.

But that’s why I keep making stuff. I use my self-criticism as motivation. It gets me out of bed. It forces me to write. It helps me record podcasts. My self-criticism humbles me. I know I’ll never be as good as I’d like to be. How good I’d like to be is galaxies away from who I am today. My future self and my current self are made out of different DNA.

I keep making stuff because I can’t stop shitting my pants.
(And because leftovers taste terrible.)

A call to action that won’t bode well on LinkedIn



Shit your pants. Shit your friends pants. Shit your parents pants.

Wherever you go, leave a big, stinky pile of shit in your wake.

Keep shitting over and over wherever you go, and eventually your shit won’t smell so bad.

Further reading for the budding self-critic

  1. Seth Godin is one of my favorite writers. Everyday he shares his timeless wisdom on creativity, life, and business. His post The world’s worst boss is my favorite piece on self-critique. Highly recommended.
  2. The War of Art by Steven Pressfield. Putting off your dreams? Not anymore.
  3. Anything and everything spoken by David Goggins.

I shared a draft of this post on my newsletter. Subscribe to get more thoughts on creativity, art, books, and self-improvement. New issues every Sunday morning.

Where are you hiding your bad ideas?

You’re afraid to move forward because you’re afraid of criticism, well-meaning or otherwise.

You’re afraid of criticism because you’re too attached to the ideas you generate, rather than as the generator of ideas. Being a “generator of ideas” doesn’t excuse you from generating bad ideas. Bad ideas are as unavoidable as death.

The best way to move forward is to recognize this duality. To show up to create something, share it, and bear all the mockery, nitpicking, and critique.

As if

I started publishing everyday almost a year ago. I would have started earlier, but my fear of crickets held me back.

I started writing as if one person cared. One imaginary person is all it takes to overcome that first hurdle. Once you’re after that, writing everyday becomes a war of attrition.

Whatever step you’re putting off in light of a larger goal, do it as if it matters.

Write your first post as if you have an audience. As if a crowd of people are showing up to your door every morning to hear what you have to say. Record your first podcast as if what you think matters. Work out as if taking care of yourself matters.

Do everything as if it matters, and eventually you’ll see that it does.

*As of December 13, 2020

I feel like this is barely a blog post

Because writing is hard. (Who starts a sentence with because?)

Writing is hard not because (am I using that word too much?) typing is hard, or because words are hard. Writing is hard because thinking is hard.

We like to think we think. But we don’t. We feel.

Want proof?

I’m sure you’ve heard hundreds of people say, “I feel.”

I feel, you feel, we feel. When we say, “I think,” what we mean is, “I feel.”

We’re always feeling around, touching stuff – with our brains, apparently. We rarely think. And thank God for that, because if we thinked all day we’d never get anything done. We’d just be sitting, thinking, thinking and pondering and wandering around inside ourselves. Nothing would get done. And we would die. And that would be bad.

Feeling is easy. Like I said before, everyone does it. We do it so much that we take it for granted.

Writing can be like feeling. If we practice enough. If we’re patient enough. If we’re ready.

Kevin Rapp: How to Be A Cynical Optimist (#31)

Listen on Spotify | Listen on iTunes | Watch on YouTube | Trailer

Today I’m joined by hardware engineer and comedy writer Kevin Rapp. Kevin writes a weekly newsletter about nothing, aptly titled the “Full of Krapp newsletter.” I’m subscribed to dozens of newsletters. Kevin’s is by far one of my favorites. It’s part hysterical part informative take on the ridiculousness of modern life. Highly recommended.

We cover:

  • Comedy, what it is and why it matters
  • Kevin’s favorite comedians (and some of mine)
  • The outrageousness of outrage culture
  • People who get compared to Hitler who shouldn’t be compared to Hitler
  • Writing advice
  • Glue, horses, and how they’re (not) related
  • Criticism and how nobody avoids it (even Viktor Frankl)
  • The draconian California lockdown curfew
  • And loads more.

Please enjoy!

Listen on Spotify | Listen on iTunes | Watch on YouTube | Trailer

Every Sunday, I write a weekly newsletter full of advice for creatives, plus extra goodies like drafts of blog posts and previews of the podcast. Sounds good? Click here to subscribe and get the next issue delivered straight to your inbox on Sunday.

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!

Impostor syndrome makes no sense

The accountant who’s writing a novella behind their boss’s back feels “safe” behind a spreadsheet than on a call with a publishing house. “I’m not an accountant,” they say. And yet they show up everyday to keep being one.

We’re less fraudulent doing something we hate, and more fraudulent doing something we love.

This makes no sense.

The prototypes of your dreams

You wanted to create something, but you had no idea what or how or why.

And then something inside you lit up like a bonfire.

You started recording, writing, designing, hiring. Working.

What was once a flash of insight turned into something tangible. People noticed. And you were even congratulated for your effort.

But then you hit a wall. Today’s numbers were the same as yesterday’s. What gives? Where did your momentum go? “There must be something fundamentally wrong about my approach,” you say. Distraught, you tear it down, scrap it, and fill up your trash bin with the prototypes of your dreams.

Finally, you start over from square one. A clean white board. A blank canvas. A fresh start.

There’s a simple alternative.

As my buddy Greg points out, overnight successes take a very long time. Resist the temptation to start over from square one. Instead, lay down the next brick. And the brick after that, and the brick after that…

I like big words

Much writing advice discourages big words. This advice is mostly geared towards new writers. New writers like to sound smart. And so they decorate their paragraphs with verbose cacophony that’s harder to decipher than a corporate apologia. But we know that people who are actually smart explain stuff with clouds, cats, dogs — the kind of symbolism even a dolt like me can understand. And so we’re told that simple language is best.

But there’s a difference between decorating your point with jargon and explaining with eloquence. And if we need to look up a word in a dictionary, is that the writer’s fault, or ours? What’s wrong with having a rich vocabulary?

Use as many big words as you want.

Just be honest about why you’re using them.