Rachel runs a small product business that offers high-end home goods. She has loyal customers and steady online sales.

Last January, she set her big goal for the year: launch a wholesale channel. Get her products into 20 boutique stores by December.

She had it mapped out. The objective was clear. The key results were specific: sign 20 retail partners, generate $150K in wholesale revenue, maintain 40% margins. Her systems were solid: reach out to 10 stores per week, attend two trade shows, create a wholesale catalog.

By March, she'd signed three stores. By May, seven. She was on track.

Then June hit.

Her manufacturer had a quality issue. Product delays. Then her biggest retail partner that accounted for 30% of her wholesale revenue went out of business. Suddenly she was behind, scrambling, and questioning whether wholesale was even viable.

"I don't know what I did wrong," she told her mentor. "I had a plan. I executed the plan. And it still fell apart."

Rachel didn't do anything wrong. But she planned for everything to go right, and nothing ever goes completely right.

The problem wasn't her goal or her execution. The problem was she never asked: "What could go wrong? And what will I do when it does?"

Planning For Failure Is Absolutely Critical

Most advice about failure planning sounds like pessimism dressed up as strategy. But there's neuroscience behind why it actually works.

Research covered by neuroscientist Andrew Huberman shows that when you visualize only success, you get a short dopamine spike that feels good but fades quickly. Your brain treats the visualization like you've already won, which actually reduces your motivation to do the work.

But when you visualize failure, specifically, when you mentally rehearse what could go wrong and how you'd respond — your brain releases dopamine, epinephrine, and acetylcholine. These neurochemicals heighten alertness and learning readiness. You're building neural pathways for problem-solving before the problem hits.

The research shows that "foreshadowing failure" nearly doubles the probability of achieving a goal compared to focusing only on success.

That's not pessimism. That's preparation.

The tool for doing this systematically is called a pre-mortem.

The Pre-Mortem Process

A post-mortem analyzes what went wrong after failure. A pre-mortem assumes failure before you start, and identifies what's most likely to kill your goal.

Step 1: Set your goal

Use the OKR + Systems framework. Get clear on what you're trying to achieve.

Step 2: Assume total failure

Fast-forward to the end of the quarter. Write this down: "It's [end date]. We failed. We didn't achieve [objective]."

Step 3: Brainstorm what caused the failure

Get specific. Ask:

• What external factors could kill this? (market, competitors, suppliers, customers)

• What internal factors could kill this? (execution, team, resources, assumptions)

• What hidden assumptions might be wrong?

Rachel's list included: manufacturer couldn't scale, retail partners wanted exclusivity she couldn't offer, 60-90 day payment terms killed cash flow, a major partner went out of business owing her money.

Step 4: Prioritize by likelihood and impact

Rate each potential failure on likelihood (low/medium/high) and impact (low/medium/high). Focus on anything that's high in either dimension.

Rachel's high-priority risks: cash flow from slow-paying retailers, manufacturing partner can't scale, margins don't support wholesale economics.

Step 5: Build mitigation strategies into your plan

For each high-priority risk: "What can we do now to prevent this or reduce its impact?"

Rachel's mitigations:

• Cash flow risk: Require 50% deposit on first orders. Build 90-day cash buffer before scaling.

• Manufacturing risk: Qualify a backup manufacturer before launching.

• Margin risk: Set a hard floor—if margins drop below 35%, pause expansion.

Rachel's Revised Plan

Same objective. Smarter execution.

Revised Key Results:

• Sign 10 retail partners (down from 20—realistic for year one)

• Generate $75K in wholesale revenue (reflects smaller scale)

• Maintain 35% margins minimum (clear floor)

• Keep DTC revenue flat or growing (protects core business)

Built-in Failure Plans:

• If margins drop below 35%: Pause acquisition, renegotiate with manufacturer

• If a retailer goes 60 days past due: Stop shipments, move to cash-on-delivery

• If DTC revenue drops 15%: Reduce wholesale outreach 50%, refocus on core

• If manufacturing partner can't deliver: Activate pre-qualified backup

By December, she'd signed 12 retailers (beating her revised goal), generated $85K in revenue, and maintained 36% margins. The manufacturing issue still hit—but because she had a backup qualified, she switched within three weeks instead of three months.

Did everything go perfectly? No. Did she hit her original ambitious goal? No.

But she built a sustainable wholesale channel without killing her business. That's not failure. That's intelligent execution.

Do This First

This week:

1. Pick your most important current goal.

2. Write: "It's [end date]. We failed to achieve [objective]."

3. Spend 15 minutes brainstorming: What could have caused this failure? Be specific.

4. Identify your top 3 risks (most likely or most damaging).

5. For each: What can you do NOW to prevent this or reduce its impact?

You can't prevent every failure. But you can stop being surprised by predictable ones.

One Last Thing

Most people spend hours planning for success and zero minutes planning for failure. Then they're shocked when reality doesn't cooperate.

Fifteen minutes of pre-mortem thinking can save you months of scrambling. The question isn't whether something will go wrong with your current goal. The question is whether you'll be ready when it does.

Schedule Quarterly Pre-Mortems, Not Just Post-Mortems: Most businesses only analyze what went wrong after a project fails. Instead, build pre-mortems into your planning process. Every quarter, before you finalize your OKRs, run a 30-minute pre-mortem session. Ask: "If we fail, why?" Then build mitigations into your plan before you start. Prevention is cheaper than recovery.

Separate "Failure to Execute" from "Failure to Choose the Right Goal": When something isn't working, diagnose which type of failure it is. Did you not do the work consistently? That's an execution problem—fix your systems. Did you do the work consistently and it still didn't move the needle? That's a strategy problem—change the goal. Don't waste months executing the wrong strategy or pivoting away from the right one.

Build "Circuit Breakers" Into Your Goals: Define specific conditions that trigger an automatic pause or pivot. For example: "If margins drop below X%, we pause expansion." Or "If customer acquisition cost exceeds Y, we change channels." Or "If we're 40% behind pace at month two, we reassess the goal." These circuit breakers prevent you from blindly pushing forward when the data says stop.

Am I avoiding this pre-mortem because I'm afraid of what I'll discover?" This reveals whether you're being honest about your plan's vulnerabilities. If you resist identifying risks because it might reveal your goal is unrealistic, that's exactly why you need the pre-mortem. Better to discover the problems now when you can prepare for them than later when they're destroying your business.

"If this goal fails, will I have learned something worth the cost?" This reveals whether you're taking smart risks or reckless ones. Some failures teach you critical lessons about your market, your customers, or your business model. Those are investments. Other failures teach you nothing except "I should have been more careful." Those are wastes. Before committing to a risky goal, make sure the potential learning justifies the potential cost.

Assume things will go wrong. Identify what's most likely to break. Build your response into the plan before it happens. That's not pessimism. It's how obstacles become expected course corrections instead of devastating surprises.