Start at the End

When you’re starting something new - whether it’s a roadmap, a project, or even a single feature - it’s natural to think from the beginning: design some classes or tables, lay out an API or UI, and get moving.

But this approach often leaves gaps. Important steps get overlooked until the last minute, or the team spends weeks perfecting a piece of work that doesn’t actually connect to the rest, or delivers little in the way of additional value for the time spent.

If the beginning of your projects seem relaxed, confident and fun, and the ends are often or always stressful, you’re likely falling into this trap.

There’s a better way to deliver, and to spread that stress out in a consistent and sustainable way: start at the end, and work backwards.

Why Planning Forward Falls Short

Forward planning feels intuitive: how do you complete a journey of 1000 miles? One step at a time, right? You tend to focus on those first steps, the ones you can see clearly, and push the fuzzier, more complex items further down the line. In addition, you tend to forget the unknown but entirely predictable surprise blockers, external interruptions, and missed or late requirements that all live in that fuzzy place right around mile 999.

That’s why so many teams hit last-minute delays and end up very stressed, often resorting to “crunch” to get things over the line - testing and release plans aren’t considered early enough, less important features were built first and have absorbed valuable time, there’s no buffer for last minute surprises that every complex project encounters, and so on.

In testing this approach is referred to as “shift-left”, meaning we shift the weight of our work left or backwards in time (for LTR readers). But it applies more broadly than that.

The Strength of Backwards Planning

When you begin with the release in mind, you will far more naturally capture the steps that really matter. You know you’ll need testing. You know there’s a rollout sequence. You know sign-offs and reviews have to happen. You capture time for feature flags, config changes, release cycles, release dependencies - all that noisy mess that happens at the end.

Take the time to sit and visualise the first user interaction with your feature. How did they find it? Was it happenstance? A tutorial, or an e-mail? Ok, and if the feature is there, how did it get there? Did you just click a button to release? Or are you flipping a feature flag in some configuration? Continue to work your way back - if you are flipping a flag, that means you set up the flag. And that means your code is aware of the flag. What if you need to flip the flag back? Ok, you’ll need time to ensure your code works the old way and the new way. How do we tell our user what happened if we roll it back and the feature suddenly disappears? And so on.

Not only does this process help you and your team build a plan that captures important steps that tend to go missing until the last minute, but it helps to put your scope and estimates in a realistic light - often we intuit estimates based on build time and difficulty, alone, and forget that it’s not just code that’s being written here, a product or feature is being shipped, and there’s much more to it.

This is because we naturally tend to think forwards, from zero to something, instead of from the goal back toward zero - that “something” is all-too-often only part of the story.

Writing Documents Backwards

This principle can also help you with technical writing. Generally, we write how we think: from zero to something; from idea to proposal; from hypothesis to conclusion. But this is not how people read.

One of the simplest ways to level up your technical writing and have it land with broader audiences is to write it backwards: start with the conclusion, or the proposal, then work backwards to how you got there. Let’s take an example - perhaps you are proposing a project based on an opportunity you’ve identified. Here’s the “forwards” way of writing, a very natural way:

Background
Hypothesis
Data
Conclusions
Options
Proposal

For many readers, they won’t know if the work is worth their time to read until they get to that very last point in the document. So let’s flip that:

Proposal (chosen from ->)
Options (supported by ->)
Conclusions (drawn from ->)
Data (based on ->)
Hypothesis (motivated by ->)
Background

What this does, in a way, is “sort” the document in “ascending order of detail”. Technical documents are not novels, we aren’t reading for the pleasure of discovering the ending. Readers are often busy and want to know upfront what this document is all about, “just get to the point”. And then, sometimes, that point is interesting enough our reader may want to know why we think this way, what lead us to this idea - and all they have to do is keep reading as we slowly add more detail, until they lose interest.

Starting at the end means the point you’re trying to make lands immediately, and doesn’t risk the reader’s eyes glazing over before it arrives.

Building Software Backwards

This principle also works at the technical level. Instead of building every individual component or feature first and attempting to integrate them later, start with the simplest possible end-to-end flow and get it live if you can. Hide it behind a password, or a feature flag - whatever method is appropriate.

Testing in production (safely, behind flags or walls) is not just acceptable, it’s often preferable. Although, in theory, we’d love clean development and/or staging environments that perfectly replicate production, there are many and legitimate reasons (e.g. legal, privacy, etc.) why this is impractical or even unachievable in many organisations. Testing in prod is ok - what matters is that you’re not testing on your users (without their permission, of course).

It doesn’t matter if this version just prints “hello, world” everywhere, has no-op implementations of everything, and is slathered in // TODOs. What matters is that you can run the whole system from start to finish. Once that’s in place, you can iterate with confidence - filling in functionality piece-by-piece, always seeing that it fits together as a working whole, and always having something available to communicate progress, garner feedback, and facilitate testing.

This helps you and your team focus on outcomes instead of isolated tasks, and aids to prevent getting lost in the weeds when a subtask blows out unexpectedly (and one always does).

Summary

It’s human nature to start with the easy or interesting work. Doing the first task on the list, writing the Background section, or building the simplest component in the spec all have that dopaminergic allure of ticking something off your list. But this is almost always the wrong approach. By starting with the end and working backwards, you naturally front-load the hard and essential parts that make complex delivery and communication possible.

It’s the same logic behind “eat your vegetables first” - the discipline to start with the less appealing, but more “nutritious”, work first will ensure you don’t “fill up on junk” and leave no room for the important stuff. This approach will set you apart from your peers and enable you to tackle projects many others couldn’t.

Here’s the key things to remember:

Plan Backwards: forward planning puts stress at the end; backward planning evens it out.
Spoil the Ending: technical documents are not novels, so don’t keep readers in suspense.
Flow before Feature: build the simplest end-to-end flow first, then worry about filling in the features.
Eat your vegetables: focus on the boring, hard or uncertain steps before the fun, easy or known ones.

At first this process feels uncomfortable, even counter-intuitive. But with practice, it becomes second nature - and soon you’ll wonder how you ever did things any other way.