Break My Plan?

Find the weak spots in your plan before they find you.

Have a plan you're about to put into action? Describe it and Break My Plan? will work backward from an imagined failure to find the weak assumptions, warning signs, and failure paths worth thinking about now — while you can still do something about them.

See what Break My Plan? gives you

Real output from an actual run on the plan below. Part of the result is shown; nothing is reworded.

The plan

Quit my agency job in June to go freelance as a UX designer, with two current clients who have said they would follow me as the base. Stakes: Six months of savings and a mortgage. If it fails I go back to the market a year older, with a gap. Assumptions: The two clients actually follow. I can bill about 60% of my hours. I will not mind selling.

Real run, 2026-10-08 — one of the tool's own built-in examples.

Test this assumption first

The two clients actually follow you when you leave the agency. Both clients have said they would follow. What is not yet known is whether those conversations were formal commitments, informal encouragement, or something in between — and whether their ability to contract with you directly depends on agency agreements, procurement rules, or internal approval that has not yet been tested.

Most likely way it fails: Client commitments do not convert to contracts

  • Why: Clients who genuinely want to keep working with you may still face internal procurement rules, preferred-vendor lists, or agency non-solicitation clauses that prevent them from contracting with you directly, regardless of intent. Good intentions and actual contracts are not the same thing.
  • Reduce the risk: Before giving notice, have a direct conversation with each client about the mechanics of contracting with you independently — not just whether they want to, but whether their procurement process permits it and what it would take. Aim for a signed agreement or at minimum a written statement of intent before you hand in notice.

Early warning signs

  • One or both clients delays confirming a specific first engagement — meetings happen, intentions are restated, but a signed brief or purchase order does not arrive within the first few weeks of your start date.
  • Your actual billable hours in the first month fall noticeably short of the 60% target, and the shortfall is not explained by a one-time setup period you had already planned for.

When to reconsider

If, by the time you give notice, neither client has signed a contract or issued a formal engagement letter with you personally — or if one has gone quiet — the financial foundation is not yet real. Delay the June quit date until at least one client is contracted and paying, or reduce your fixed costs enough that the savings runway extends materially beyond six months. Do not treat verbal enthusiasm as equivalent to a signed agreement.

In a Nutshell

When
The plan is written and everyone agrees. That's the dangerous moment.
You give
The plan in specific terms and what type it is.
You get
The assumption your plan leans on most, the warning signs to watch, and what to change now.
The edge
It works backward from failure to find the assumptions forward planning skips.

Good to Know

Questions people ask

What is a pre-mortem?

You imagine the plan has failed and work out the most likely reasons, before you start. It surfaces risks that optimism hides, while there's still time to change the plan.

How do I know if I'm ready to go freelance?

Turn your assumptions into things you can check: signed contracts instead of promises, a realistic share of billable hours, and how many months your savings cover your fixed costs.

Will it tell me not to do it?

No. It shows how the plan could fail, what to test first and the signs to watch for, so the decision stays yours.