How to stop doubting yourself as a beginner Substacker
#2: A few simple ways on how to fight that inner voice persuading you to quit
It felt great when I hit that publish button on my first Substack post yesterday.
But today, it’s a completely different story.
For some reason I woke up at around 2am. I couldn’t fall asleep again. And I felt like a miserable zombie.
After lying in bed, at around 4am I finally decided it was high time to drag myself out of bed.
I drank some water and went for my usual morning walk.
I didn’t want to lie there like a vampire in a coffin, staring at the ceiling and listening to the sob stories of my inner bitch complaining about today’s to-do list and how tired I’d feel later if I didn’t go to sleep.
The funny thing is, the more I thought about having to go back to sleep, the more awake I felt. I couldn’t stand it, so I just decided to get up and break this ridiculous inner bitchery and nagging—put on clothes and shoes, didn’t even wash my face, just walked out.
I wanted to leave that inner voice behind, but it echoed in my mind for a good few hundred metres as I walked:
“Today you’re running the trading desk on your own, you’re working from home—you should have slept longer.”
“It’s Friday! You deserve a longer sleep.”
“Alex is staying with Sheila, you didn’t have to get him ready for school. Relax.”
“It’s a work-meeting day. You’ve got the bank. You have to be rested—go back to bed.”
“It’ll be a long day. You need to food shop later—Alex is with you this weekend, remember?”
“You need to cook, too. And don’t you dare eat pizza—you’re fat, pizza isn’t healthy, you’ve just lost 20kg and you’ll kill all your progress.”
“Plan a nice father-and-son weekend while you’re at it.”
“Short sleep tends to raise cortisol.”
“It’s going to be a long day—why the f*ck are you not sleeping?”
Arrgh!
Just a few more steps.
The voice was finally gone.
I won the first fight.
But the war was far from over.
As I carried on towards Colindale—my regular morning running route—and passed the shuttered Colindale station, the inner bitch came back. Double strength. This time from a different angle.
It went straight for my weakest spot: my Substack, where I’d just posted my first article.
I’ve committed to free-writing and publishing every day for the next 100 days, and I intend to stick with it.
But on that walk, I couldn’t stop turning the commitment over, and I had a fiery argument with myself that nearly talked me into quitting.
How the heck am I going to stick to an article a day?
I’ve got enough on my plate—work, bills, co-parenting, the lot.
I started doubting myself.
And worse, the whole walk became one long internal row with that inner bitch, trying to talk me out of my little writing dream.
I was almost ready to give up. But when I got home, took a cold shower, brewed coffee, opened my laptop and muttered let me just open Substack and start a new draft—something shifted.
I started flipping through my notes—my Daily Journal, and a notepad titled Writing & Concepts where I jot down ideas I like as I read or watch things.
And as I gathered my thoughts—whoosh, an idea.
Why not put the spotlight on that inner bitch? Drag the voice of doubt into the open, break it into pieces, and look at it properly.
So if you’re going through the same thing—that little voice starting to whisper, trying to drag you off your Substack, your writing, your small dream—let’s fight it together.
Today I’ll do my best, with my ambition and my beginner’s toolkit, to work through three questions:
What is self-doubt, really?
Why do you doubt yourself as a beginner?
How do you get past it and just do your thing?
What is self-doubt, really?
When I sat down to write this after an hour-long scrap with self-doubt—my mind reached for a lesson from Don’t Believe Everything You Think by Joseph Nguyen.
Nguyen draws a sharp line between a thought and thinking. A thought is something you have—it’s a noun. Thinking is an act—a verb—the act of engaging with that thought.
When you’re inspired to do, achieve or try something, it arrives as an inspiring thought. Then you overlay your own opinion and judgement, and the energy changes.
Let’s try it.
Stop for a moment.
What’s something you’ve dreamed of doing but haven’t done?
Pause. Let the answer surface. Sit with that first thought—notice how it feels.
Now dig deeper.
What would it take to make it real? Why haven’t you done it yet? What’s holding you back?
Look at what just happened. The first question pulled up a thought—an inspiration, something exciting. But the follow-ups, the ones about what’s stopping you—did you feel the shift? Heavier. Flatter. Maybe frustrated, maybe afraid. Your answers turned negative and judgemental.
For me, Substack is something I hold close. It’s my little experiment to reconnect with a childhood passion.
Now I’m trying to turn that inspiration into something real. But I didn’t manage it for years — back when I was younger, a student with fewer responsibilities, no kids, switching jobs like gloves — and I still never sat down and posted regularly. So with a track record like that, what are the odds I pull it off now?
Thought = a neutral observation, or an intuitive prompt.
Thinking = the negative story you wrap around it.
The takeaway: our small dreams arrive as thoughts of inspiration. The more we ruminate instead of act, the more reasons we manufacture to talk ourselves out of them. We overthink ourselves out of starting.
Why you doubt yourself as a beginner
You have your dream. You’re inspired. You’re trying to make it real.
And right now you’re a beginner who, frankly, doesn’t know much yet.
You see other Substackers—thousands of followers, essays you couldn’t have written, a rhythm you can only imagine.
You see where you are. Between here and there is a gap. A scary one. It can’t be jumped in a single leap. It takes work. Sweat. And fighting that inner bitch every day she crawls out to bite you exactly where it hurts—in the dream.
That gap is normal. Your taste is already sharp — sharp enough to see how far your writing falls short of it. The skill just hasn’t caught up yet. That’s not a reason to stop. It’s the reason to keep going.
If you’ve got a small dream—like me, to write on Substack—don’t think. Execute. The longer you ruminate, the less likely you are to start.
As Steven Pressfield puts it in The War of Art:
“It’s not the writing part that’s hard. What’s hard is sitting down to write. What keeps us from sitting down is Resistance.”
And the only way to prove to yourself—and to her—that you’ll get what you want is through action.
How to get past it: seek momentum
Now you’re thinking: “easier said than done, Jack.”
Fair. So here’s the practical bit.
The only way to pull the dream off is to start. Action gets you rolling, and once you’re rolling you build momentum. That’s why I free-write—no blueprints, no Substack-guru playbook, no “10 steps to your first 1,000 subscribers”.
Most advice hands you a tidy step-by-step path. A safe one. Where you don’t actually act—you just call reading about it progress. You proudly label studying as moving forward.
Think about it. Who gets results first—the person who reads about lifting for six months, planning diets and dreaming about the perfect trainers, or the one who starts today with ten sit-ups, showing up whether they’re a sleepy zombie or not?
Thought so.
So how do you practise showing up?
Two ideas help, and they’re not the same one.
The psychologist B.F. Skinner called the first shaping—you don’t wait for the whole behaviour to appear and then reward it. You reward the small steps that point towards it, one rough approximation at a time, until the full thing takes hold.1 For a writer that doesn’t mean “write a brilliant essay”. It means “open the laptop”. Then “write one line”. Then “publish something — anything”. Each small step is the win.
James Clear comes at it from the other side. His third law of behaviour change is simply make it easy: cut the friction until starting takes almost no effort.2
If you want to be a writer, you have to write. To write, you have to show up—regularly—until it’s just what you do.
And to make showing up easier, cut the friction. Make the habit as small and effortless as possible. I cut my own friction by telling myself: all you have to do is open the laptop. Then I write—freely, no topic, no title, whatever comes, go with the flow, don’t worry, just write and publish. You’ll be fine.
Free-writing is how I practise showing up, in the easiest possible way. My laptop sits in the same room as my bed. My running shoes are right next to it—all I have to do is put them on and walk out. If they were in another room, I probably wouldn’t bother. The extra few steps would be enough of an excuse.
So—did I win the war this morning? You’re reading the answer. The inner bitch had me for most of the walk. She nearly had me at the laptop. But the gap between losing and winning turned out to be one small action: opening the lid and starting a draft. That’s it. That’s the whole trick. Tomorrow she’ll be back, double strength, from some new angle. And tomorrow I’ll open the laptop again. One more day. That’s all this ever is.
So next time, if you ever doubt yourself:
Recognise the fact that doubt is just a product of your thinking and you don’t have to listen.
Do the absolute minimum, but don’t throw up a zero—show up.
Show up, until you feel that wind of momentum.
Take it slow—one day at a time.
Do your thing,
Jack
B.F. Skinner, Science and Human Behavior (Macmillan, 1953).
James Clear, Atomic Habits (Avery, 2018).