The Awkward Middle
Why Passion Always Gets Hard — And Why That’s a Good Sign
“Extraordinary benefits accrue to the tiny minority of people who are able to push just a tiny bit longer than most.” — Seth Godin
I stared at my computer screen, the words a total blur. Had I really written this?
Just a few months earlier, I’d been in Joshua Tree for my first solo writing retreat, finishing up some chapters for a book I’ve been working on for the past few years. Sunrise writing sessions in a dusty coffee shop, long hikes, tacos each night at the local saloon — by the end, I was certain: I’d never written anything better.
So when I reread those same pages a few weeks ago, I wasn’t expecting to cringe. But the writing felt stilted, guarded, nothing like the voice I wanted — or even how I sounded in my own head. My stomach dropped. For a moment, I just stared. Had I really changed that much in a few months? Or was I just simply too close to see it clearly at the time?
No big deal, I told myself. I’ll do a quick rewrite. The bones were good; it just needed my voice back — a few days’ work, I thought.
Days of work turned into weeks, and soon, I was pacing around at my local coffee shop, feeling like I was spinning in circles. Every sentence felt stiff and wrong. Embarrassment turned to frustration, then to full-on panic. I bought five books on writer’s voice and editing, desperate to figure out what was going on.
That’s when it hit me: I’d landed squarely in the awkward middle stage — what psychology calls conscious incompetence. I’d been working steadily to improve my writing, so in retrospect, it wasn’t a big surprise I’d finally hit a wall. But at the time, it felt like all my progress had vanished overnight, replaced by self-doubt and the creeping fear that I was actually getting worse.
And here’s the thing: every real passion will drag you here eventually.
Why We All Get Stuck Here
I’ve been obsessed with skill development for as long as I can remember. Years ago, I stumbled onto the “Four Stages of Learning,” first mapped out by management researchers at NYU in the 1960s. The model quickly took hold in sports psychology, business, coaching, and adult learning — fields obsessed with getting better on purpose.
But even though you won’t hear about it much in creative writing workshops or art schools, I’ve found it applies just as much to creativity or any deep passion. Writers, artists, and musicians live this cycle every day, even if they never put a name to it.
And it’s not just pop psychology. Variations of this framework show up everywhere — from research on expertise and deliberate practice to the way psychologists and coaches help people push through that inevitable “why am I so bad at this?” phase. It fits every passion I’ve chased: writing, jiu-jitsu, handstands, drawing, building companies, even learning how to lead a team.
The big thing: passion and skill are inseparable. If you stick with something you’re passionate about for long enough, you’ve almost certainly felt these stages — even if you didn’t know their names.
Here’s how the cycle plays out:
Unconscious Incompetence: This is the blissful beginner phase. You don’t know what you don’t know yet, so everything feels possible and even small wins feel huge. These are the first few exciting points you score in a pickleball game, the first chords you learn on the guitar, the few lines you write in your novel that don’t totally suck.
Conscious Incompetence: Then comes the crash. Suddenly you see how much you have to learn. This is the “I suck” stage. It’s what most people confuse for being an awkward beginner, but if you’ve made it here, congrats — you’re actually making progress. You know enough to see your own gaps.
Conscious Competence: With enough practice, you start to get the hang of things. You can pull off a triangle choke, hold a handstand, write a coherent chapter — but you have to focus hard. Progress is real, but it’s fragile. Everything still takes a lot of effort and intention.
Unconscious Competence: Finally, you stop having to think so much. The skill becomes unconscious. Now you’re flowing, improvising, maybe even teaching others. You might even forget how hard it once was.
Of course, none of this is a one-time ladder to climb. As you continue to learn and build skills, you’ll go through these stages, over and over. If you stick with anything long enough to matter — to become a real passion — you’ll hit every stage above, often more than once.
What if Awkwardness is a Sign You’re on the Right Track?
Most people think the pain of starting something new is the hardest part. But beginnings are usually fun — there’s low pressure, everything is novel, and wins come easily. It’s only after those early gains fade that things start to get hard.
This is the stage where most people give up, where the Passion Dip happens, and where most passions fizzle. Paradoxically, it’s also the only place where much real growth happens.
When I look back, the skills I’m proudest of aren’t the ones that came easy — or even the ones I mastered. It’s the things I kept showing up for: rewriting a chapter twenty times before it finally felt true, fumbling through jiu-jitsu moves until they stuck, grinding through the slow, hard parts of turning an idea into reality. I’ve hired coaches, devoured books, watched tutorials — anything to shortcut the struggle. But there’s only ever one way forward: you keep going.
Science backs this up: Dunning-Kruger, deliberate practice, adult learning theory — they all point to the same truth: if you’re stuck in the messy middle, where everything feels worse before it feels better — congratulations. You’re on the path. The only real mistake is quitting before the magic happens.
I try to remind myself of this every time I wrestle with the middle of writing my book. Awkwardness is normal. It’s part of it. And it will get better — as long as I keep going.
So if you’re stuck in your own awkward middle, doubting your path, wondering if you’ll ever make it out — don’t back down.
That struggle means you care enough to keep going, even when it’s hard. That’s where real passion — and real progress — are born.