How to Plan a Software Project Without Losing Your Mind

I had a call last week with a new client. Super sharp guy, building a pretty complex WooCommerce extension for syncing inventory with a third-party API. He was completely stuck. He’d been coding for three months, had a laundry list of features, but nothing was actually finished. His project board was a mess of vague tasks like “Build the admin dashboard” and “Handle API authentication.” He felt like he was churning constantly but never actually shipping anything. Total paralysis. He didn’t have a feature problem; he had a planning problem. He needed a real product development framework, not just a to-do list.

The core of his issue is something I see all the time. Devs think of work in horizontal layers: design, then backend, then frontend. You map out all the design, then all the database tables, then all the API endpoints. It feels organized, but it’s a trap. You end up with a bunch of half-finished components that don’t actually form a usable feature. Nothing is ever done done.

Trust me, I’ve made this mistake myself. My first big project, I tried to fix the chaos by creating a massive JIRA board. I broke “User Profiles” into 20 tiny tickets: one for the database schema, one for the REST endpoint, one for the avatar upload component, one for the form styling… you get the picture. It was a masterpiece of micromanagement. The problem was, at any given time, we had 10 tickets “in progress,” but for weeks, there was no usable profile page. It was a total nightmare and the team lost motivation fast.

A Better Way: Vertical Scopes of Work

The real fix is to stop thinking horizontally (by role) and start thinking vertically (by feature). The goal is to define a self-contained slice of work that delivers a complete piece of functionality, from UI to database. I’ve refined my approach over the years, heavily influenced by a couple of concepts I first saw discussed over on carlalexander.ca. It’s a mix of working backward from the end goal and packaging the work into what Ryan Singer from Basecamp calls “scopes.”

Instead of a “User Profile” project, you define a scope called “Users Can Edit Their Own Profile.” That scope isn’t just a single task; it’s a checklist of everything required to make that one sentence true. When the scope is done, the feature is fully integrated and works.

Example Scope: Basic Stripe Integration

Let’s say you’re adding payments. A horizontal plan would have tasks for “Design checkout form” and “Create payments API endpoint.” A vertical scope is different. It looks like this:

  • Goal: User can pay for a single product via Stripe.
  • Tasks:
    • Design a minimal, one-field credit card input form.
    • Add a `Pay` button to the product page template.
    • Write the server-side endpoint that receives the form post.
    • Integrate the Stripe PHP SDK to create a charge.
    • Handle success: Redirect to a simple “Thank You” page.
    • Handle errors: Display “Payment failed, please try again.”

Once you check off all those items, that scope is 100% done. It’s a tangible, testable piece of the final product. No lingering front-end work, no disconnected back-end code.

So, What’s the Point?

This isn’t just about project management theory. It’s about momentum. Every completed scope is a win for the team and a concrete step closer to launch. It forces you to make decisions about what’s essential for the feature to simply work, pushing all the “nice-to-have” stuff to a later scope. You stop getting bogged down in endless details and start shipping finished features. Even if they’re small. Progress. Finally.

Look, this stuff gets complicated fast. If you’re tired of debugging someone else’s mess and just want your site to work, drop my team a line. We’ve probably seen it before.

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