Fail before you fail: How pre-mortems save projects

What if you could spot the cracks in your project before everything falls apart?

Pre-mortems let you do exactly that. They’re not about overthinking every “what-if” but about addressing the obvious risks you already know are lurking.

For freelancers — who don’t have teams to back them up or a buffer for failure — this is a lifesaver. It’s your chance to save yourself from unnecessary chaos and sleepless nights.

What’s a Pre-Mortem?

You’ve probably heard of post-mortems: those meetings where teams dissect what went wrong after a project crashes and burns. Useful? Sure. But not exactly proactive.

A pre-mortem flips this idea. Instead of waiting for failure, you pretend it’s already happened. You imagine your project has gone spectacularly off the rails, then figure out why.

This isn’t about doomsday scenarios. It’s about common sense: identifying weak spots early so you can avoid turning small cracks into major disasters.

Why Freelancers Should Care

Let’s face it: as a freelancer, you’re your own safety net. No one’s going to catch your oversights, smooth over client issues, or remind you about that one thing you forgot to follow up on. Pre-mortems help you safeguard your work — and your sanity.

Here’s why they matter:

• You’re the last line of defense. There’s no one else to double-check your work or pick up the slack.

• Clients love foresight. Spotting potential issues before they happen builds trust and shows you’ve thought things through.

• They save time. Avoiding problems early means fewer late nights scrambling to fix them.

• They give you confidence. Knowing you’ve handled the risks frees you up to focus on the work, not the what-ifs.

The OH SH-T Framework

Outcomes, Hazards, Solutions, How-to.

This is the four-step framework for freelancers who need to stress-test their projects without overthinking or overcomplicating.

Why the name? Because this is what you won’t be saying once you’ve run it…!

Outcomes

First, get clear on what success looks like. Write it down in one sentence, no jargon.

For example: “Deliver a logo and brand guide the client loves, within four weeks.”

Ask yourself:

• What exactly am I delivering?

• What will success look like for me?

• What will success look like for the client?

Hazards

This is where you embrace your inner pessimist and imagine everything going spectacularly wrong. Be vivid.

But here’s the hack: Instead of listing risks generically, write out the text you’d send to your best friend when each disaster happens:

• “Fuck me. My client just said ‘This draft is totally wrong, we need to start again,’ and they’re pissed.”

• “I completely underestimated how long revisions would take. Now it’s 2am, I’m 2 coffees and 1 wine down, and have zero energy.”

• “Soooo they still haven’t paid me, and the project is 80% done. WTF.”

Prompt yourself with:

• What could go wrong with the client? (expectations, sudden changes, payment issues, timezone differences, different generation, multiple stakeholders, etc.)

• What could go wrong with me? (procrastination, overbooking, etc.)

• What could go wrong with logistics? (tools, timelines, payments, etc.)

Solutions

For every hazard, write down one specific thing you can do today to stop it from happening. The key here is not just “what could help” but rather: “What action solves this problem now?”

For example:

• Hazard: “The client hates all the concepts and demands a redo.”
  Solution: “Show rough drafts of 3 concepts in Week 1 to get early feedback.”

• Hazard: “The timeline is crunched, and I’m stressed.”
  Solution: “Add two buffer days into every deadline I propose.”

• Hazard: “Payment hasn’t arrived, and I’m working for free.”
  Solution: “Request 50% upfront before starting any design work.”

How-To

FINAL STEP! 😄 Take what you’ve mapped out and turn it into a quick-reference plan. Write it somewhere you’ll actually see it — stick it on your fridge, pin it to your Asana board, or save it in your project notes.

Keep it simple:

1. Your outcome (1 sentence)

2. The hazards (bullet points)

3. The solutions (what you’ll do to prevent them)

The big question I’m sure you have is probably: “Do I share this with my client?”

Yes: If your process needs buy-in — things like deadlines or feedback timelines — then this is a great way to show them you’ve thought ahead. You gain trust, they gain confidence that you’ve got your ducks in a row. And they get a gentle nudge to not f*ck it up.

No: If you know your clients are a bit sensitive or risk-averse, or if you have no read on whether they’d appreciate a pre-mortem or not, then it might be worthwhile keeping it as a reminder for yourself.

If you’re totally unsure: Give ChatGPT a buzz, and chat it through there. Make sure to give loads of context about the client, the project, and your OH SH-T worksheet. And then ask it for an analysis on how to decide whether said client should get this thinking or not!

An Example in Action

You’ve landed a branding project for a startup. The client needs a logo, brand guidelines, and social media templates—all in six weeks. Here’s how the OH SH*T Framework helps you stay on track:

1. Outcomes — What Are You Actually Doing?
Deliverables: logo, brand guidelines, and five templates.
Outcome: “Create a cohesive brand identity the client loves in six weeks.”

2. Hazards — What Could Blow Up?

• “The client keeps asking for extra deliverables—scope creep.”

• “Their idea of ‘modern’ doesn’t match mine—unclear expectations.”

• “I didn’t leave room for revisions—timeline crunch.”

3. Solutions — What Can You Fix Now?

• Add clear revision limits and extra costs into your contract.

• Use a questionnaire to align on style upfront (e.g., “What brands do you admire?”).

• Pad the timeline with feedback deadlines and buffer days.

4. How-To — Keep It Front and Centre
Write your plan down where you’ll see it—your fridge, Asana board, or project notes. Use it to guide decisions, stay proactive, and show clients you’re ahead of the game.

When to Use a Pre-Mortem

Here are some great trigger-moments where pre-mortems can be especially helpful — note them for yourself!

• Between proposal and contract phase, in order to spot hidden risks before you’ve contractually agreed on anything

• At any point in a project where new challenges or “icks” arise

• When working with a brand new client

• When working with a client you know can be tricky to manage

• When working in new territory (in terms of skills, industry, or company-size)

The Bottom Line

Pre-mortems aren’t about paranoia; they’re about preparation. They help you anticipate risks, impress clients, and avoid unnecessary chaos.

So, the next time you’re planning a project, ask yourself: “How could this fail?” Then make a plan to stop it from happening.

Run the OH SH*T Framework before your next project and thank yourself later. Or don’t—and enjoy sending those “help” texts at 2 a.m. 😉