Your One Job as a Beginner: Screw Up Constantly
The only proven path to rookies becoming veterans
My kids are watching the Yankees and trying to become better baseball players.
While it’s adorable, there’s a real problem trying to learn baseball from Aaron Judge.
He’s blasting 420-foot bombs into Monument Park. He’s robbing home runs at the warning track. He’s gunning down baserunners from right field in ridiculous fashion.
My kids, by contrast, kind of stink.
Of course they do. They’re 6 and 4. Both can hit decently. Gloves occasionally find batted balls. Throws sometimes hit their marks.
But Aaron Judge, they certainly ain’t.
The 4-year-old is still blissfully ignorant. But the 6-year-old is measuring himself against his teammates who were All-Stars last year. The gap frustrates him.
He’s learning a valuable lesson that we tend to forget as adults:
Starting anything new is a pain in the ass.
The Familiar Pattern of Starting
Starting something new—whether it’s a diet, a musical instrument, or learning a new language—follows a very familiar pattern.
We get excited about the idea. We envision a future where we’re ripped at the pool, shredding guitar on stage, or ordering dinner in Spanish while visiting Spain.
We build a plan to learn the new skill. We figure out the diet and training program, sign up for guitar lessons, or download the new language app. LFG. We’re ready.
We start. Early on, it’s fun to be a beginner. Our mind is expanding to see how much of this thing we don’t know. We’re going to learn so much! Noob gains galore! This is freaking awesome. We are now more interesting humans than we were before beginning our journey.
That lasts about a couple of weeks…maybe more, maybe less. Then we hit a wall. Thanks to author Steven Pressfield, I now know the name of that wall (more on that in a minute). Maybe you keep working through it. But what started as fun now feels like work.
At some point, momentum dies. We slip up. We don’t practice guitar because we have friends in town. We miss a day on the Spanish app (and break our streak…dammit). We skip a workout or inhale a cheeseburger because we’re so goddamn sick of kale already.
Now comes the guilt. “Another thing you gave up on.” “You can’t stick to anything.” “You said you wanted this!” And guilt is the gateway to shame.
If you’re like me, the descent into the shame spiral comes with some truly inspiring self-talk:
“Guess you’re wearing a shirt at the pool this summer, fatso.”
“Who’d you think you were gonna be, Stevie Ray Vaughan? Stay in your lane: power chords and Blink-182 covers.”
“Get ready to mumble your order of vino and jamón in English, you tourist.”
Eventually, we stop feeling guilty altogether. It’s just this thing we don’t do anymore. We put the guitar in the closet. We delete the app—or worse, leave it there to bully us daily, “because one day we’ll come back to it.” We buy one-pieces and cover-ups for the summer.
We’re back in our usual routine. The vision for what we were trying to achieve is dead. And most of us don’t even know what killed it.
Meet Resistance
If you’re a fan of author Steven Pressfield (and if you’re not, you should become one), you know the name of the force we’re up against. In The War of Art, a must-read book for anyone trying to create anything in this world, Pressfield personifies the enemy most of us don’t even know we’re fighting:
“Most of us have two lives – the life we live, and the un-lived life within us. Between the two stands Resistance.”
Pressfield’s core premise is this: Resistance is the most insidious, persistent force working against your potential. It will find a way to keep you stagnant—whether through distraction, perfectionism, rationalization, or fear. And if you’re starting something new, ambitious, and important to you, bet your ass you’ll encounter it.
Resistance will tell you anything to keep you from doing your work. It will perjure, fabricate, falsify; seduce, bully, cajole. Resistance is protean. It will assume any form, if that’s what it takes to deceive you. It will reason with you like a lawyer or jam a nine-millimeter in your face like a stick-up man. Resistance has no conscience. It will pledge anything to get a deal, then double-cross you when your back is turned. If you take Resistance at its word, you deserve everything you get. Resistance is always lying and always full of shit.
This force is always at its most disruptive when you are getting into a project you care about. It’s the urge to check your phone when you sit down to write. The pull to buy a new pair of Jordans instead of getting building your business plan. Letting Netflix carry you into one more episode at night as you adjust the alarm on your phone, wiping out the morning workout.
And don’t think he’s being cheeky or sarcastic: Resistance is lethal. It’s also terrifying because it moves in silence. It’s nearly impossible to detect in the micro. Decision by decision, delay by delay, you give up little moments of your life. Minutes turn to hours, turn to days, turn to weeks, turn to years.
And then, you reach the end of the line. Your life’s work never came to pass. And one of your final thoughts will be, “How did I end up here without doing what I was meant to do?”
This is how Resistance kills you: by silently robbing you of your life.
What My Resistance Looks Like
I’ve been trying to build this thing for over a year. Since I’m not mega-viral or mega-rich, it’s fairly obvious I’ve been getting a lot of it wrong.
I’ve been trying to build this thing for over a year. Since I’m not mega-viral or mega-rich, it’s fairly obvious I’ve been getting a lot of it wrong.
I choose the wrong topics to write about. I can be ineffective at translating my thoughts to the digital page. I write stuff that feels great when I post it, just to watch it die on the vine. I curse the algorithm gods, just to re-read my work a few days later and think, “Well, that deserved to be buried...it sucked.” Resistance bloodies my nose, then laughs at me when I retreat to re-strategize.
Because that asshole knows what I know: strategizing isn’t writing.
Writing is writing. Creating is creating. Whenever I’m not bringing something to life, Resistance is winning.
Since launching the 2nd Act Launchpad earlier this year, the violence has continued to escalate. I pull a knife; Resistance draws a pistol. I reach for a rifle, Resistance pulls out a bazooka. I don’t even bother to find a tank, because I know that’ll invite a drone strike.
I built a business to help people build their own businesses...but my own build has been one big brawl with this monster. I got damn near everything wrong. I made mistakes that I was actively coaching people not to make. I didn’t effectively use the tools I built to help others.
I’d journal every night, trying to untangle what I was doing wrong. Resistance would whisper, “Who the hell are you to say you can help people? You can’t even get this shit right on your own.” I’d slam the journal shut, defeated, wondering if it’s too late to get rich by learning how crypto works.
Another frustrating day that didn’t move the needle on my goal (or so I thought).
How To Defeat Resistance
“I cannot lose if I do not quit.” - Alex Hormozi
I heard that quote while wading through a 3-hour Modern Wisdom episode. This was sometime in the doldrums of the content creation struggle, so likely tail end of summer 2025. It hit me at a time I needed to hear it.
A few days later, that sentence was still bouncing around my mind. I wrote it on a notecard on my desk so I could see it every day. When I cleaned the desk a week later, I transferred it to my whiteboard.
It’s still there. Nearly a year later, it’s my mantra. It turns out, it’s also Resistance’s Achilles heel.
When you start something new, everybody tells you that you’re going to suck at the beginning. “Maybe those other people did,” your ego whispers, “but I’m going to nail it.”
But you don’t nail it. Worse: you faceplant. Turns out, starting is actually hard, and sucking is the prerequisite to success.
At this point, you have a choice: keep trying, or give up. I like Seth Rogen’s quote on this:
“If you don’t quit, you might make it. And if you quit, you definitely won’t.”
That’s the whole secret to beating Resistance and achieving your goals in two sentences.
Just don’t quit.
Does this mean I have it all figured out? Hell no. I’m still scratching and clawing my way to 10k followers on LinkedIn, falling behind on this newsletter, and experimenting with YouTube. I’m also helping my first cohort of 2nd Act Launchpad members start their businesses, distilling decades of recruiting, leading, and mentoring into an AI-fueled coaching experience. There’s no playbook for that, and I’m making the requisite mistakes to get good at it.
But while I’m growing, I’m watching my clients, quietly and uncomfortably, suck at stuff, too. I recognize their clumsy steps—because they were the clumsy steps I took. I share the same advice I heard early on (and ended up being true): “It’s OK, you’re supposed to suck at the beginning. Keep going.”
I’m finally giving Resistance some bruises. The war rages on, day after day, never gaining a true advantage, but keeping the beast at bay. I’m still in the arena. And that qualifies me to share the only effective battle plan I’ve found to win:
Step 1: Try. Fail. Try again. Fail again. Repeat over and over until you see the first sign of progress.
Step 2: Repeat Step 1.
Because you cannot lose if you do not quit.