The million-dollar question most people never ask

Hey there, my friend!

This week during our family holiday in Bad Gastein, something fascinating happened.

While my family discussed their New Year's dreams around the breakfast table, I noticed a pattern so clear it stopped me mid-bite.

Everyone had big dreams. Beautiful dreams.

But they all started their sentences the same way:

"Someday, when..." "Once I have..." "After I..."

Sound familiar?

See, watching them, I realized something interesting about success and dreams that I never understood during my finance days in Singapore.

Here's the thing - most professionals aren't stuck because of skills or strategy.

They're stuck because they're asking the wrong question.

Let's dive in.

Here's the million-dollar question most people never ask:

"What would you do if you knew you couldn't fail?"

Not "should do." Not "need to do." Not what looks good on your performance review.

But what would you actually create if success was guaranteed?

When I left my finance job, everyone asked "how?"

• How will you make money?

• How will you start over?

• How will you succeed?

But here's what I've learned:

The "how" is killing your dreams.

Quick story:

In Singapore, I met dozens of brilliant people. Ivy League degrees. Six-figure salaries. Corner offices.

All of them waiting to figure out "how" before taking action.

Most of them dying inside, one Excel sheet or Power Point presentation at a time.

Here's what changed everything for me:

Success isn't about having all the answers. It's about taking action before you're ready.

Look at what happens when you stop asking "how" and start taking action:

Walt Disney? Fired by a newspaper editor for "lacking imagination." Now his name defines imagination.

Fred Astaire's first Hollywood screen test: "Can't act. Can't sing. Balding. Can dance a little." He framed that rejection and hung it in his mansion after becoming a legend.

See the pattern?

The greats don't wait for permission. They don't wait for the perfect "how." They move before they're ready.

I learned this firsthand:

My first AI project? Complete flop.

Second attempt? Even worse.

Third try? Actually made money, but felt hollow.

But each "failure" taught me something the corporate world never could:

The only real failure is waiting for perfect clarity.

Success isn't about perfect planning.

It's about imperfect action.

So what does this mean for you in 2025?

Here's your blueprint for breaking free:

1. The Truth Game

   Tonight, grab a notebook and write down the dream that scares you most. (You know the one - it pops into your head when your quarterly review feels empty)

2. The Fear Flip

   Next to each fear, write this: "But what if it works?"

Not: "What if I fail?" "What if I look stupid?" "What if it's the wrong move?"

Just: "But what if it works?"

3. The One-Day Rule

   Take ONE action toward your dream within 24 hours.

• One email

• One phone call

• One small step

Why 24 hours?

Because your brain needs proof that you're serious. Your dreams need evidence that this time is different.

Remember:

• Henry Ford failed three times before the Model T

• J.K. Rowling got rejected by 12 publishers

• Steve Jobs got kicked out of his own company

They all had one thing in common: They moved before they were ready.

Your AI Action Step

I've crafted a specialized ChatGPT prompt to help you break through your "how" barrier and start moving toward your dreams.

Here's how to access it:

1. Visit ChatGPT (https://chat.openai.com/)

2. Copy and paste the following prompt

3. Fill in your specific situation

4. Watch as AI helps you navigate your challenges

As a Success Pattern Navigator, your task is to break down big dreams into actionable steps by analyzing the user's current situation.

[Insert your current role and dream]

Map out the following elements for the user:

- **Three small action steps**: Identify three specific, actionable steps the user can take within 24 hours to move towards their dream.
- **Potential initial roadblocks and solutions**: Recognize common obstacles they might encounter initially and suggest quick solutions.
- **Past successes**: Highlight the user's past successes that can boost their confidence in pursuing this dream.
- **Key skills**: Identify the user's existing skills that align with and support their dream.
- **First signs of progress**: Describe early indicators that will show the user they are on the right path.

Encourage immediate action over perfect planning, using direct but supportive language.

# Output Format

Present the output as a structured list with subheadings for each of the mapped elements. Include a short, actionable statement for each action step, a list of roadblocks with solutions, and concise statements for past successes and key skills. The first signs of progress should be presented as a brief, descriptive paragraph.

HOW TO USE THE PROMPT

Here is the output I received for the example inputs above.

Read the full output here!

Final Thoughts From Bad Gastein:

Sitting here in the Austrian mountains with my family, watching snow fall on fresh beginnings, I'm reminded of something powerful:

Every success story starts the same way. Not with clarity. Not with certainty. Just with courage to take that first, imperfect step.

Right now, somewhere in Singapore, someone's sitting in the same office I left, dreaming the same dreams you have.

The only difference between those who make it and those who don't?

One group waits for permission. The other group starts before they're ready.

Which will you be in 2025?

To your courage,

Stephan

P.S. Hit reply and tell me: What dream are you ready to start this year?