I learned about common mistakes in startup planning the same way I learned not to microwave aluminum foil.
By doing it.
And then standing there like, “Wow. That was… preventable.”
If you’ve ever sat on your couch at 1:12 a.m., laptop open, tabs multiplying like rabbits, thinking this one feels different, congrats—you’re my people. I’ve planned startups on napkins, in Notes apps, in my head while brushing my teeth. Some plans were decent. Some were… aggressively confident for no reason.
And listen, I’ve had a decent run. A few hundred blog posts. Some flops. Some surprises. People liked enough of them that I kept going. But the planning mistakes? Oh, those were consistent. Almost comforting in their predictability.
So this post isn’t a lecture. It’s more like me sliding into the booth across from you, lowering my voice, and saying, “Okay. Don’t do this thing. I did it. It hurt.”
Let’s talk about the big ones about common mistakes in startup planning.
Mistake #1: Planning for “Everyone” (Instead of One Real Person)
This one gets everyone. Including me. Repeatedly.
Early on, my target customer was:
“Anyone who wants to improve their life.”
Which is adorable. And useless.
When you plan for everyone, you connect with no one. Your messaging gets vague and features balloon. Your brain hurts.
The fix?
Pick one painfully specific person.
Not:
- “Small business owners”
But:
- “Solo freelancers who hate selling and procrastinate invoices until panic sets in”
When you plan for that person, decisions get easier. Marketing gets clearer. And weirdly, more people end up relating anyway.
Counterintuitive. Annoyingly true.
Mistake #2: Falling in Love With the Idea (Instead of the Problem)
I’ve done this more times than I want to admit.
I’d get attached to the idea. The name. The logo (oh god, the logo). I’d defend it like a toddler protecting a toy.
Then someone would say:
“I don’t really have that problem.”
And I’d internally whisper, yes you do.
Nope.
Good startup planning obsesses over the problem, not the solution. Problems stick around. Ideas evolve.
If people aren’t actively annoyed by the thing you’re solving, planning more won’t save it.
I wish it did. It does not.
Mistake #3: Overplanning the Product, Underplanning the Distribution
Confession: I once had a 22-page product plan.
Distribution plan?
One sentence: “We’ll market it.”
Sir. How.
Data (and heartbreak) show this clearly: startups don’t fail because the product is bad. They fail because nobody shows up.
Better planning question:
- How will the first 100 people hear about this?
If you can’t answer that without saying “ads” or “going viral,” pause.
Distribution isn’t an afterthought. It’s half the plan.
Mistake #4: Assuming Motivation Will Carry You
Ah yes. Motivation. That fickle little gremlin.
I used to plan startups assuming Future Me would be:
- Disciplined
- Energetic
- Immune to Netflix
Future Me is… not those things.
Good planning assumes:
- You’ll get tired
- You’ll doubt yourself
- You’ll want to quit
So you plan systems, not willpower.
Simple systems beat big goals:
- Weekly check-ins
- Tiny milestones
- Accountability (even if it’s just a friend who side-eyes you lovingly)
Motivation fades. Systems stick around like that one song you didn’t mean to memorize.
Mistake #5: Ignoring the Money Stuff Because It’s “Not Fun”
This one makes people squirm. Me included.
Early planning often sounds like:
“We’ll figure out pricing later.”
Later comes fast. And aggressively.
You don’t need a CFO-level model. But you do need to know:
- What costs money
- How much runway you have
- What needs to work for this to survive
I once planned a startup where the math never math-ed. I just… hoped it would. It did not.
Money clarity doesn’t kill creativity. It keeps it alive.
Mistake #6: Confusing Planning With Progress
This is a sneaky one.
Planning feels productive.
Color-coded docs. Roadmaps. Tools.
But planning isn’t progress. It’s preparation.
I’ve seen people plan for six months and avoid:
- Talking to customers
- Shipping anything
- Testing assumptions
At some point, planning becomes procrastination in a blazer.
A good rule:
If your plan doesn’t force you into contact with reality soon, it’s too comfortable.
Reality is messy. But it’s where answers live.
Mistake #7: Treating the First Plan Like a Sacred Text
Your first startup plan is not a prophecy.
It’s a guess.
And guesses are allowed to be wrong.
Early me would cling to plans like:
“But this was the plan!”
Yeah. And now you know more.
Good founders update plans. Bad plans get defended. There’s a difference.
If new info shows up—and it will—adjusting isn’t failure. It’s competence.
Planning is a living thing. Not a tattoo.
A Quick Side Rant about common mistakes in startup planning
Planning doesn’t need to be perfect to be useful.
It needs to be honest.
Honest about:
- What you don’t know
- What scares you
- What assumptions you’re making
I should probably be embarrassed, but honestly? Some of my best decisions came after admitting, “I actually have no idea what I’m doing here.”
Clarity comes after action more often than before it.
🔗 Outbound Links Worth Clicking
- Paul Graham’s essays (especially the early planning ones)
- Wait But Why for perspective when your brain spirals
The Real Point of common mistakes in startup planning
Planning isn’t about predicting success.
It’s about reducing regret.
You’ll still make mistakes. Different ones. New ones. Fun ones.
But if you can avoid the obvious traps—the ones everyone falls into—you give yourself room to learn instead of recover.
And honestly? That’s the whole game.
