🌴277. The Hidden Power of Quitting feat. Alan Weiss (Weekend Rewind)

This week on Talk the Walk, Alan and I riff on quitting—firing clients, pausing projects, and stopping things that technically “work” but don’t work for you anymore. We dig into ego, sunk-cost traps, scope creep, and how to communicate a graceful stop without burning bridges. Alan shares a simple pre-flight test to help you avoid quitting later by deciding smarter upfront.

In this episode

• Why “don’t be a quitter” is terrible advice for grown-ups with goals
• Alan’s 5 When-Not-to-Start filters (my new decision cheat sheet)
• Preventing scope creep with pragmatic curiosity (ask before you say yes)
• Temporary quits, partial quits, and getting help to stop
• Feedback without pity: choosing truth-tellers and being one
• Sunk costs vs. smart experiments (market first, build later)
• How to cancel or pause publicly without drama (and keep goodwill)
• What consultants should quit immediately (hello, time-sink social!)
• Raising value before raising fees (Peloton did this well)
• The monkey bars analogy: you can’t reach out unless you let go

My takeaways

• Ask a better first question: not “Can I help?” (always yes), but “What’s in it for me—learning, growth, low labor, fair revenue?”
• Five red flags = don’t start: low interest, little learning, no growth path, poor revenue, excessive labor.
• Curiosity saves you later: clarify sites, scope, timelines, decision rights before you commit.
• Quitting can be temporary: pausing ≠ failing. Partial stops count.
• Truth > cheerleading: select 2–3 people who’ve proven they’ll tell you the truth.
• Market → then make: sell the outcome, then build the content once you have critical mass.
• Value drives fees: explain the added value before you adjust price.

Favorite moments & quotables

• “If you never let go, you’ll never reach out.” (Monkey bars!)
• “It’s better to ask when not to start than wonder when to stop.”
• “The way to be successful isn’t to raise fees—it’s to raise value.”
• “Be empathetic with feedback, never pitying.”

Tiny scripts you can steal

• After you blurted ‘yes’: “On reflection, I’m not the right person for you. I can suggest the kind of expert who’d be a better fit.”
• Cancelling with class: “We don’t have critical mass for the learning dynamic. I won’t waste your time—I’ll let you know if we reschedule.”

Shout-outs & references

• Hugh Jackman (Alan’s NYC weekend plans!)
• Peloton’s price-rise email framed through added value
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