How to make progress when starting something new

Executive overview

Starting something new rarely goes to plan. The gap between your initial idea and where you actually need to go is almost always wider than expected.

The path forward combines small experiments (firing bullets) to find the right target, drawing on past history for courage, and building conscious practices that sustain momentum.

• Your dominant self-story may be working against you — find a better one.
• Experiments fail cheaply; skipping them makes cannonballs miss.
• The transition from experiment to practice is about consistency, not habit automation.

You unlock your greatness by working on the hard things.

Firing bullets before cannonballs

• A bullet is a cheap, low-stakes test to find where the real target is.
• A cannonball is a full commitment — only load it once bullets have confirmed the target.
• Two failure modes: firing the cannonball before testing, or firing bullets forever out of fear of commitment.
• Most people can only see in retrospect that they were firing bullets — it rarely feels rational in the moment.
• Useful cadence: six-week cycles to test, learn, and recalibrate without catastrophic cost if a cycle fails.

Using your history to find courage

• When facing something new, ask: when have I faced something like this before?
• Your dominant story about yourself may be inaccurate and actively unhelpful — surface a different one.
• Example: self-publishing the coaching habit as a professional, with full investment in standards and process, contradicts the "high-performing amateur" narrative.
• Peak-moment stories remind people of essential parts of who they are that get buried in daily life.
• The "you are..." exercise: a listener reflects back six things they observe in someone sharing their peak story — the receiver just says thank you.

Designing a good experiment

• An experiment moves you forward on a worthy goal while keeping risk low.
• It answers: what small thing could tell me something useful and keep me safe?
• Experiments are range-finding — the goal is to get close enough to the real destination, confirm it's right, then head for it.
• Avoid making experiments too large or too emotionally invested in a specific outcome.
• Once you arrive at a milestone, stop and ask: what do I now know that I didn't before?

Transitioning a company to new leadership

• Hired an external coach (Jill Murphy) for the year before and year after Shannon Minnifee became CEO of Box of Crayons.
• Created a decision tree based on Susan Scott's twig/branch/trunk/root framework:
  • Twig: CEO handles, founder never hears about.
  • Branch: founder learns in regular updates.
  • Trunk: CEO decides, but consults founder first.
  • Root: founder's decision alone.
• Founder kept only two root decisions: sell the company, or fire the CEO.
• When the new CEO changed core company values, having the framework made it possible to stay out rather than interfere.
• Coming to peace with the possibility of failure — the company might not survive — was essential to giving the CEO genuine authority.

Experiment versus practice versus habit

• Experiment: trying things out, still searching for what's right.
• Practice: you've found the right experiments; now doing them consistently and consciously.
• Habit: behavior pushed into the unconscious — you stop noticing the act itself.
• The value of a practice is staying conscious: meditation where you are watching the breath, not just breathing.
• Example practice: pre-interview research — a two-page briefing note, then time to generate personal, deeper questions rather than surface-level ones.

Conscious incompetence as a growth lever

• The four stages: unconsciously incompetent → consciously incompetent → consciously competent → unconsciously competent.
• High achievers tend to structure their lives around areas of mastery, avoiding conscious incompetence.
• Seeking out conscious incompetence — deliberately doing something you're bad at — is what cracks open the next stage of growth.
• Consuming content (podcasts, books, talks) is only the start; action inside discomfort is where deep learning happens.

Identity shift as the final step

• Changing what you do is insufficient without changing what you call yourself.
• Example: owning the label "writer" rather than defaulting to teacher or businessperson — even after writing multiple bestselling books.
• Asking "what would need to be true for me to be able to do this?" forces the identity question into the open.