The Challenge of Choice:
29 Days to Better Decisions
and a Better life
A Follow-Through Program that turns insight into lasting clarity, confidence, and better choices — in just 10 minutes a day.
INTRODUCTION
29 Days to Better Decisions and a Better Life
Week 1: Waking Up to the Power of Choice
Exposing the silent killers of Success
Day 1 - The Real Cost of a Bad Decision
Behind every regret is a decision you thought was good – until it wasn’t.
Day 2 - You're Not as Rational as You Think
Your brain is wired for shortcuts – not sound deliberate judgment.
Day 3 - The Invisible Forces Driving Your Choices
“You’re” not always the one behind the wheel.
Day 4 - Why “Good Intentions” Aren’t Enough
You can’t out-care a bad decision.
Day 5 - Behind Every Regret Is a Decision
One should not evaluate a decision by its outcome – but by the process that led to it.
Day 6 - The Myth of Experience: Smarter Doesn’t Mean Safer
Your greatest strength can become your greatest weakness when you stop questioning what you know.
Day 7 - The Leadership Choice: Take Responsibility for Your Decisions
True leadership begins the moment you stop blaming circumstances and start owning your choices completely.
Week 2: See the Hidden Traps
How biases, heuristics, and faulty assumptions derail our decisions.
Day 8 - System 1 Thinking: Fast, Intuitive, and Often Wrong
Why even smart people make bad decisions – spotting the biases, shortcuts and traps before they sabotage you.
Day 9 - System 2 Thinking: Slower, Smarter—but Lazy
System 2 – the mental muscle that can save you… but you “gotta” use it!
Day 10 - The Halo Effect, Anchoring, and the Trap of First Impressions
Your brain’s lightning-fast judgments feel like insight, but they’re actually mental shortcuts that can cost you everything.
Day 11 - How Confirmation Bias Shapes Your Reality
Your brain is not a neutral observer of reality – it’s an advocate for whatever you already believe.
Day 12 - Loss Aversion: Why You Stay in Bad Situations Too Long
The courage to walk away is often key to moving forward.
Day 13 - Overconfidence and the “I Would Never Do That” Fallacy
The very belief that you’re the exception makes you the rule.
Day 14 - Your Brain’s Blind Spot: Why You Can’t Trust Yourself
The most dangerous decision-maker is the one who believes they’re immune to making bad decisions.
Week 3: Master the Process
A repeatable decision-making framework
Day 15 - The Seven Steps to the Anatomy of a “Good” Decision
Good decisions aren’t accidents – they’re the result of following a proven, systematic process.
Day 16 - Frame the Right Problem – Or Solve the Wrong One
The question you ask determines the answer you get – make sure you’re solving the right problem.
Day 17 - Zoom Out: The Power of the Outside View
Your “unique” situation may not be as unique as you think.
Day 18 - Walk Around the Decision in 3D
Good decisions require seeing the complete picture – not just the angle that feels right.
Day 19 - Rule-Based Thinking: Your Bias-Proof Shield
Make one decision now so you don’t have to make 100 later.
Day 20 - Pre-Decisions: Why Rules Beat Willpower Every Time
Outsmart your future self by deciding before it counts.
Day 21 - Your Decision Filter: Values, Identity, and Long-Term Thinking
Filtering decisions through your values and long-term vision.
Week 4: Apply and Adapt
Making Decisions with Complete Confidence
Day 22 - Deciding in the Real World: Emotions, Ego, and Stakeholders
It’s a tricker decision when emotions run high, egos are on the line, and everyone’s watching.
Day 23 - When You Don’t Know What to Do — Decide How You’ll Decide
In certain moments, the smartest move isn’t always choosing what to do – it’s choosing how you’ll make the decision.
Day 24 - The “What If I’m Wrong?” Test
Great decision-makers don’t just ask, “What if I’m right?” – they stress-test their thinking by asking, “What if I’m wrong?”
Day 25 - Decision Journaling: Build a Feedback Loop
You can’t improve what you don’t track. Decision journaling creates the feedback loop your brain needs to get better.
Day 26 - How to Evaluate a Past Decision (Without Regret)
Don’t judge a decision by its outcome – judge it by how it was made.
Day 27 - What “Good” Decision-Makers Do Differently
“Good” decision-makers don’t have perfect foresight – they have better habits, better questions and better discipline.
Day 28 - The Critical Decisions That Define Your Life
Most of your life’s trajectory comes down to a handful of decisions – and you now have the tools to handle them with complete confidence.
Day 29 – The Decision-Maker You’ve Become
You now have something most people will never possess: a systematic understanding of how to make choices when it matters most.
The Next Step is a
Conversation
Whether you’re planning a conference, leadership retreat, or organization-wide initiative, the next step is simply a conversation about what you need and how I can help.