From chaos to connection: Embracing audacity and ease on your creative path
How embracing authentic connections, ambition, and easeful growth (rather than an easy path) can unlock your creative potential and transform your publishing journey.
This speech is adapted from the opening keynote I gave at the Future of Publishing Mastermind in March 2025.
Good morning,
I will try to be brief, but if you’ve ever listened to any of our courses or podcasts, you know that brief is a relative term. I told Mel and Tawdra I would be brief and they said “That’s what you said last year, and you talked for an hour”, but just know it is my intention.
And what better way to be brief then to start with a story from 20 years ago. Before I got into publishing, I wanted to direct movies so much that I made one. It wasn’t particularly mind-blowing, and it wasn’t particularly long, but we did make it and you can watch it. We’re coming up on the 20th anniversary of production on that movie, and until this event it was easily the hardest thing I’ve ever done.
Now, it’s not even close. This is easily the hardest thing I have ever done, and I have been channeling my inner Glennon Doyle for months. We can do hard things, Glennon. We can do hard things.
We’ve been working on this conference with focused attention for two years. Each event is 51 weeks of anxious prep for one week of (hopefully) awesome release. We have a bunch of wild ideas, pull the ones that won’t (immediately) bankrupt us together, and hope it all works out.
It’s hard, y’all, which probably isn’t too surprising if you’ve ever tried to edit an anthology, or even just tried to get your kids to agree on where to go for dinner. It’s often like herding cats.
As such, I spend a lot of time complaining about how hard it is; to Monica, to Mel and Tawdra, to my wife, to friends, and to literally anyone that will listen. I am from the east coast y’all, surrounded by Italian and Jewish aunts. I am a world-class kvetcher.
Then, one time, I was complaining to a friend that I just wanted it to be “easy”, and they replied. “Respectfully, that’s bullshit.”
“I mean rude,” I said. “But say more things about that.”
“Well, you write fiction in a genre (almost) nobody reads, and actively avoided tropes for years that would make your work more accessible. The fact you make any money on fiction is a minor miracle. You chose to get into comics even though even fewer people read them than your very niche books, made movies back before we had studios on our phones, and refuse to relaunch courses even if you could make hundreds of thousands of dollars by doing so for reasons that make no sense for any business that wants to make actual money. Basically every decision you make is designed to make your life harder.”
Again, rude, but fair. I’m really feeling seen at this moment and I hate it.
“Let me ask you,” they said. “Did anyone ask you to make a conference?”
Seriously, just so rude, right? But no, I just thought it would be a fun challenge. Isn’t that what everyone does?
Turns out no. Most people make business decisions based on ROI, or financially upside potential. Whoops. It was really an eye-opening experience, and I wish I was kidding about that, I really do.
There was a long silence before they said. “So, you chose, of your own volition, to do one of the hardest things there is to do in business, because you thought it would be a fun challenge?”
And like…just so fucking rude.
“Listen, there’s nothing wrong with easy,” they continued. “Lots of people want easy, but you’re not one of them. You want things to be easeful, not easy. Easy is without difficulty, but easeful is without friction.”
Yes, my friend chose violence that day, but they were right, too, and I’ll bet every one of you is at least a bit like me, because to get into this room you probably needed to make a lot of choices that contradict having an easy life.
You picked publishing for one, which like you don’t really need any other reasons besides that? But also you probably made a series of choices, from the genre you write to the platforms you choose to focus on to the audience you built, that at least once made people go “You shouldn’t do that. It’s going to make your life harder”, and yet you did it anyway.
It’s okay. This is a safe space to feel called out, but still…just so fucking rude.
The people that tend to resonate with our message are the ones who took the weird, circuitous route to success instead of the well-trodden path and somehow succeeded anyway.
Your career has been a lot of things, but it was not easy. If you’re in this room, you probably don’t want any easy life, but you do want a more easeful one.
Life isn’t easy for any creator because the very act of creating something exists in direct opposition to to the universe’s natural entropy. It wants chaos and destruction. Meanwhile, we harness that chaos and impose some form or order and meaning on it.
As creators, we are tasked with standing in the middle of a raging storm and shouting “Cool storm, bro, but like, can you buy my book? There’s kissing in it!!!”
Every time we do that is a little act of rebellion, and every time we create makes it just a little bit more easeful to do it again, but it is never easy. I’ve written a lot of books and not one of them has ever been easy.
Some of them have been easeful, and that’s the energy I want to embody moving forward. It might need to be difficult, maybe even complicated, but it doesn’t have to be brutal.
That is an audacious goal, considering that we’re living in the middle of chaos right now, but gods forbid we be ambitious, right?
I love ambition, and have no problem extolling its virtues, which by itself is a radical act. In a world that expects us to be satisfied with our lot in life, I strive to make sure my reach always far exceeds my grasp.
In the recent past, somewhere between a week and a decade ago (because what is time anymore), I was walking through a creator market and met an author who pitched me their book and told me how great it was.
They convinced me to buy it, I took it home, and I got angry, y’all. Honestly, I did. Books don’t make me angry, often, but this book got deep under my skin. It wasn’t bad, it was just a big bowl of nothing, like every choice they made was the beigest one possible.
And yet this author looked me in the eye and told me it was worth my time and money.
I got mad, not because of them, their book, or even their audacity, but because I know dozens, hundreds of authors who write incredible books (many in this very room), who don’t have one fraction of that author’s audacity or belief in their work.
That’s partly what I wish for you, moving forward. I actually have two wishes for you. Audacious, right?
First is the audacity to look people in the eye and not just say, but really believe, that your books are worth the time and money readers spend with them. I wish you the audacity of somebody who was never told they couldn’t do something and so they didn’t know they shouldn’t expect good things to happen when they try something.
Second, I wish you the compassion and empathy of somebody who has seen too much and wants to make sure others don’t have to suffer like you suffered, and I wish you those qualites without having to go through that suffering to find it.
Basically, I wish you the ability to do no harm but take no shit.
Before I go, I want to give you two pieces of advice about how to get the most from this experience. The first is that every single one of you has a lock and a key. I know you do because I personally approved every one of your applications with Monica. If you don’t trust your own ability, please trust in our taste, which is impeccable.
Your key will not open your own lock, but there is a key here held by somebody else that will unlock your lock, and your key will unlock somebody else’s in return.
Let me give you an example of this. Last night, I sat down across from an author and we got to talking. Soon after, somebody sat down and asked them “Hey, when are your non-fiction books going to be in audio?” Almost immediately, they got to talking about how they were very busy and didn’t have the time, but heard about how you can clone your own voice now and make AI audiobooks that sound like you, and that they wanted to look into it.
My eyes lit up, because not only had I just done this twice, but I had a VA who basically handled the whole process for me. On top of that, my VA was coming to the conference! I offered to connect them, saving the author dozens of hours of work and research. That’s what I mean by using your keys to unlock other people’s locks.
When I got back to my room, I made the introduction, and woke up to 3-4 emails back and forth between them. It turned out that one of my VA’s keys was to meet this author.
So, I unlocked two locks at the same time. Doing this for people is both easy and easeful. It just means you have to listen, care, and believe you have the ability to open those locks. Even if you can’t do it yourself, even just pointing them in the right direction is endlessly helpful.
There are 180 people registered for this event, and I want to everyone to use at least one key and unlock at least one lock while they are here. We don’t want to overwhelm you with information this week. We want to give you the right information and the right connections to clear your biggest block(s).
I had no idea that a month after the last event I would start a podcast with
who I only talked to for the first time a couple hours before the show ended, or that we would eventually interview the author I mentioned above, who would then come to our conference, or that I would be able to make that connection, just like I didn’t know that last year Lee and I would unlock nearly matching locks for each other.All of that is the planned serendipity and chaos magic born of coming to a show like this one. Good things will happen if you allow them to happen, but maybe not in the way you think.
The thing is that you can only match those locks by talking to lots of people, and you can only use your key if you meet the right person, which is why we gave you lovely green and red armbands. If somebody is wearing a green band, it means they are open to talk. If they are wearing a red band, or none at all, then assume it means give them some space.
If you are wearing your green armband, expect conversation. If you walk up to somebody with a green armband, expect them to greet you warmly.
I’m almost done, I swear, but in that spirit of speaking harsh truth, I have one more thing you will not like hearing.
Your best friend will not open your lock. If they could, they would have done it already. The people in your existing mastermind group will not open your lock. If they could, they would have done it already.
It’s great to meet with your besties and exchange notes later, but the people who got the most out of this event last year were the ones who stepped out of their comfort zone and met new people with different skills and interests.
You are surrounded by some of the smartest humans in this industry, and some of the most caring, who really want to help, but they don’t read minds. They need to hear your problem to know if they can help you break through it.
So, I encourage you to sit next to different people every breakthrough session, sit at new tables at meals, and meet with new people. Even if you only make 1-2 good connections a day, after a week that’s 10 more people in your network.
That doesn’t mean avoid going deep with people, but our goal, collectively, is to open as many locks as possible, and use as many of our own keys as possible, so everyone comes out of this mastermind like a rocketship.
20 years ago, I made a movie that became a webseries called Connections, and the tagline was “Make them last”. Here I am almost 20 years later, making the same pitch at the most audacious thing I’ve ever been part of by a wide margin.
And that my friends, is how we close a loop. This has been Chekov’s keynote. Don’t set up anything in the first three minutes you don’t plan to pay off in the last three.
Now, drop your shoulders, take a deep breath, and let’s dive in.
What do you think?
What’s one audacious decision you’ve made in your creative career that felt impossible at first but turned out to be hugely rewarding?
How do you differentiate between ‘easy’ and ‘easeful’ in your projects, and where do you see opportunities to shift from struggle to flow?
Have you ever found an unexpected ‘key’ from a fellow creator that unlocked a big roadblock in your work? Share your story!
In what ways do you embrace ambition, and how do you balance the desire to push boundaries with the need for self-care?
What’s one simple step you can take right now to connect with someone new (online or offline) who might have the ‘key’ you’ve been missing?
Let us know in the comments.
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What’s one audacious decision you’ve made in your creative career that felt impossible at first but turned out to be hugely rewarding?
—Enrolling, attending then graduating college. Granted, the place was a cesspool of false positives and false summits, but before attending, higher education were places set apart for elite thinkers and creative savants who were ordained by God, wealth, or both. After meeting, not only those attending, but those teaching, I realized they were mostly like me. Normal people who were full of wonder, hope, and some ambition to improve their lives. This revelation opened my eyes insofar that with the right amount of work, play, and luck, most goals are possible.
How do you differentiate between ‘easy’ and ‘easeful’ in your projects, and where do you see opportunities to shift from struggle to flow?
—Sadly I don’t. I go into situations prepared and expecting difficulty from start to finish. Admittedly, this isn’t healthy since it’s now evident (in retrospect) that many of these situations failed due to self-prophecy. So, I’m going to give your semantics some serious thought and see how it can be applied to my thinking.
Have you ever found an unexpected ‘key’ from a fellow creator that unlocked a big roadblock in your work? Share your story!
—While attending a writing course here in LA, the entire program was cathartic for me. My creative muses of old [i.e. “Fear” and “Laziness”] would’ve rebuked the idea that anything creative could be learned in a classroom, but this experience proved otherwise. For instance, the first script after finishing this course scored an 8 on the Blacklist and got me into the finals in several competitions. It even garnered some praise from a showrunner. I know full well these accolades mean spit in Hollywood, and my lack of employment is testimony to that effect, but it’s still far better than I had ever expected, and a win is a win.
In what ways do you embrace ambition, and how do you balance the desire to push boundaries with the need for self-care?
—If it feeds a desire to improve one’s craft, it’s invaluable. However, if it feeds envy, external validation, etcetera, then it’s a cancer.
What’s one simple step you can take right now to connect with someone new (online or offline) who might have the ‘key’ you’ve been missing?
—Aside from attending Future of Publishing Mastermind in 2026, I think I’m doing it now by responding to this article.
—There’s also another writing course (offered by a Substacker no less) that will get me involved with other writers since it’s done in person.
Stupid question: What the heck is a “VA”?
When I first learned about author websites, I said - hell no - I don’t have time, I don’t know how, etc. But then I just did it and it was fun and creative. The mindset shift was most important.