Win by going indirect using constraints and opponents’ force as leverage

Hard - Requires significant effort Recommended

Head‑to‑head looks brave, but it’s usually the slowest, costliest way to win. Big obstacles have big armor in predictable places. The trick is to notice where they’re not looking, where rules slow them down, or where pride makes them clumsy. The side door is often unlocked if you look for it.

Start by mapping strength and moat. A competitor might own mass advertising, but they’re slow at custom work and allergic to transparency. Or your tough class curve rewards test tricks but ignores lab coaching. Those edges are invitations.

Then set a flank objective. If one giant deal requires endless committees, target five smaller buyers who decide in a week. If public debate in a meeting is political, do the work before the meeting, one‑to‑one, and show up with allies and improved ideas. You’re not cheating. You’re choosing a game you can win.

Exploit asymmetry with speed, empathy, and openness. Reply same day, ship a sketch, show your work. When they push hard—extra forms, vague feedback, last‑minute demands—don’t push back. Pause and let the friction reveal what they value least. That’s where your leverage lives.

This approach borrows from judo and systems thinking: redirect force, avoid strongholds, and use constraints creatively. The goal isn’t to look strong, it’s to be effective. Quiet wins compound.

List where the obstacle is strongest and where it’s blind. Decide on a flank goal that avoids the stronghold and plays to your speed or empathy. Act in the gaps: publish openly, respond fast, and customize where they can’t. When pressure rises, don’t push back; let it expose a weakness you can use. Pick one side‑door move you can make this week and take it.

What You'll Achieve

Internally, you’ll drop the ego need to win head‑on. Externally, you’ll close deals faster, navigate politics smarter, and achieve results with fewer resources.

Choose the side door on purpose

1

Map strengths and moats

List where the obstacle is strongest. Then list fringe areas they ignore, slow layers, or rules they must follow that you don’t.

2

Set a flank objective

Define a success that avoids their strength. Example: win five small accounts instead of one giant one, or influence the room before the meeting.

3

Exploit asymmetry

Use speed, simplicity, empathy, or transparency to move where big players can’t. Publish openly, respond faster, or customize instead of standardize.

4

Let pressure overextend them

When they push, don’t meet force with force. Pause, reframe, and let them expose a weakness you can use—like poor service or slow cycles.

Reflection Questions

  • Where is this obstacle strongest, and where is it blind?
  • What success can I define that avoids their strength?
  • How can I use speed, empathy, or openness to exploit asymmetry?

Personalization Tips

  • Career: Instead of competing for one internal promotion, build a visible project with another team and become the obvious bridge hire.
  • Sales: Skip the RFP cage match and host a short working session that solves a real problem; win by proving value early.
The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
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The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

Ryan Holiday 2014
Insight 6 of 8

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