Why I do strategy backwards

I do strategy backwards. When explaining my approach to someone this week, it became clear how different this is from how most people work.

Many folks start with what they have today. They look at current resources, consider existing constraints, and then plan incremental steps forward. This makes perfect sense and it works.

But I've always found myself starting somewhere else entirely.

The backwards approach

Instead of moving forward from today, I imagine the best achievable outcome. Not fantasy. Not unlimited resources or breaking physics. But the best version that could actually exist in the real world.

Then I reverse engineer from there.

This quote has always been on the back of my mind:

"Imagination is the factory that makes legends. It is the beginning of all achievement. To imagine is to perceive many potential futures, select the most delightful possibility, and then pull the present forward to meet it."

That phrase: "pull the present forward to meet it" captures exactly what this backwards approach feels like.

How working backwards actually works

Here's a high level of what I do:

1. Define the best achievable outcome What would amazing look like if we got everything right? Not perfect, but the best version within reality's constraints.

2. Trace backwards from that outcome What needs to be true for that to exist? What capabilities, systems, or changes are required? Walk backwards, what does reality look like one step away from the goal, then two, then three.

3. Map the gap from today Now look at where you are. The path becomes surprisingly clear when you know exactly where you're headed.

4. Execute forward with clarity Each step has purpose because you know how it connects to the destination.

Why this creates less waste

When you work backwards from a clear outcome, you naturally filter out activities that don't contribute to it meaningfully. You're not experimenting to find your goal. You're building toward something specific and clear.

At Buffer, I practiced this to write our Engineering Direction. That's why there's not a vague goal like "improve developer experience," but rather "30 people, 300 person impact." All with specific outcomes like removing CI/CD blockers and improving our shipping cadence without negatively impacting quality.

Working backwards from that vision revealed exactly which constraints to tackle and which were distractions.

Reality is more malleable than we think

We've literally gone from caves to space stations. Not through incremental planning, but through imagination pulling the present forward.

It applies everywhere: → Team structures that seem fixed but aren't → Technical debt that feels permanent but isn't → Market positions that appear locked but aren't

The distance between where you are and the best achievable outcome is usually smaller than it appears. Most constraints are actually assumptions. Most barriers are actually design decisions.

Applying this to your work

Next time you're planning something, try flipping your process:

1. Start with the best achievable outcome
2. Work backwards to identify what needs to be true
3. Map the gap from your current state
4. Execute forward with clarity

You'll find that: → Many "impossible" things are just hard → Most constraints are conventions → The path becomes clearer when you know the destination

The trick is starting with clarity about where you want to end up.

Who would have thought that "doing it backwards" would be so positive.

This piece originally appeared in my weekly newsletter. Subscribe for insights on thinking differently about work, technology, and what's actually possible.