The Paralysis of Planning in small teams. How to break the loop
Planning as quasi-productivity in small teams
I love planning.
Seriously. Give me a task or a goal, and I will break it down into tiny, beautiful pieces. Market research, budget, business model, project timeline, roles, a clean design system, a sharp value proposition, and neat mind maps. I’m genuinely good at this.
And it feels… satisfying.
Sometimes it feels like the work is already done.
I once finished preparing a budget for a large festival and realised I felt almost as much pleasure as if we had actually run the event. In my head, everything was there: the venue, sponsors, programme, a huge audience. It all made sense. Conceptually perfect. Almost emotional.
This strange feeling — when preparation gives you a sense of completion — is what made me want to write this.
The problem: Planning as a proxy for progress
We usually think bad planning means underestimating time or resources.
But this trap is different.
You plan, and it feels productive.
You refine, revise, rearrange, and brainstorm. It feels like progress.
You get a dopamine hit from “figuring things out”.
And you delay starting the actual work.
Fabio Rosato calls this the Planning Trap: when planning becomes an end in itself, not a tool for action. Planning feels safe and controllable, while doing the work feels risky and uncertain.
Source: fabiorosato.com/posts/planning-trap
Easy Momentum puts it even more directly: planning becomes procrastination in a tailored suit. You tell yourself you’re preparing, but in reality, you’re postponing the moment when things get messy, hard, and unpredictable.
Source: easymomentum.substack.com/p/how-planning-became-the-new-procrastination
Anna Kornick connects this to overplanning and analysis paralysis: too many variables, too many scenarios, too many versions of what “launch” should look like — and nothing ever ships.
Source: annadkornick.com/overplanning-and-analysis-paralysis/
The Paralysis of Planning in small teams
Big organisations have deadlines, KPIs, managers, stakeholders, and external accountability. In a 30-person team, someone will eventually ask, “Where’s the deliverable?” And the project ships because it has to.
In small teams or solo projects (like my Make It Work), that pressure often doesn’t exist. Time and results are self-regulated. There is no weekly stand-up where you must show progress.
No boss defining what “done” means.
There’s also something else we don’t talk about enough: the fear of launching as a public act. It’s one thing to say, “Look, our team or organisation launched a project.” It’s a very different thing to say, “I am doing this.” That moment triggers impostor syndrome, fear of judgment, and fear of being seen. Planning becomes a safe hiding place. You’re “working”, but you’re not yet visible.
So the move from planning to doing becomes an internal decision, not something forced by external pressure. And that makes it much harder. Staying in the comfort zone of plans is easier than stepping into imperfect action.
This is why small teams and solo builders get stuck in planning loops more often than large organisations with formal structures.
Signs you and your team are in the planning trap
You’re stuck in planning mode. Plans keep growing, while real tasks get smaller.
You feel productive without output. Planning gives you a real sense of progress.
You feel overwhelmed by decisions and options.
Revisions beat execution. Every week, you rewrite the plan instead of building.
You’re chasing perfection before starting.
You avoid the actual work. Launch is delayed because “something is still missing”.
What to do about it
1. Time-box planning
Give planning a strict limit. For example: two hours, then stop. Everything (revision, rethinking, reflection, other amazing re’s!) only after the action
2. Use the “Good Enough” mindset
“Good enough now” beats “perfect later/never”. Feedback comes only from things that exist in the real world, not from your head. If it doesn’t directly move something into the real world, it doesn’t belong in the planning phase anymore.
3. Create a Power Hour
One hour with no planning, no optimisation, no improvements. Just action. Even if the result is rough.
4. Set action triggers
An action trigger is a rule that tells you when planning must stop and action must start.
For example:
After the first draft, I publish.
After one screen, I put the page online.
After one post, I don’t think about the content strategy.
This removes emotion from the decision and replaces it with a simple rule.
5. Add external accountability
Even if you work alone:
Make public commitments. Tell your partner that Thursday is launch day. Tell a friend you’ll show something before Friday beers.
Set weekly check-ins. A short, recurring moment where you answer one question:
What did I actually ship this week?
A small amount of external pressure helps turn intention into action.
Planning isn’t the problem. Without a plan, you’ll probably just stay stuck.
The trap is when you start confusing preparation with progress. You spend hours on a perfect Notion board or a strategy deck, and it feels like work.
A first step based on a “good enough” plan beats a perfect plan that never leaves your head every single time.