How Thinking Like a Millionaire Changed My Product Development Mindset

I was stuck in a small conference room. My product was failing. My team was tired. Everyone was mad at me.

I was making “safe” choices instead of bold ones. Playing it small instead of dreaming big.

Then I heard something that made me stop everything.

A mentor told me about a millionaire who was asked: “What would you do differently if you had to start over?”

His answer? “I would think bigger sooner.”

Right then, I knew I’d been playing way too small. Not just with my product. With my whole career.

The Truth About “Being Realistic”

Here’s what nobody tells you: How big you think decides how big you win.

When I started out, my goals were tiny:

• Ship features on time
• Fix a few bugs
• Get a small raise

But these weren’t goals. They were limits pretending to be smart.

The most successful people I know? They thought big from day one. While we built features, they built platforms. While we wanted promotions, they created jobs that didn’t exist yet.

The Broke Millionaire Who Knew He’d Make It

I heard about a millionaire who was once $100,000 in debt. But even then, he knew he’d build something huge.

Not hoped. Not wished. Knew.

“Why think small?” he said. “That’s just boring.”

This isn’t crazy talk. It’s about knowing this truth: What you have today doesn’t limit what you can build tomorrow.

The Plan: From Big Dreams to Real Results

Step 1: Pick Your “Impossible” Goal

For Your Product: Don’t say “make users happier.” Say “make something users can’t live without.”

For Your Business: Don’t say “increase revenue by 20%.” Say “build something that changes how an entire industry works.”

For Your Career: Don’t say “get promoted.” Say “become so good that companies invent new jobs just for me.”

Step 2: Build Your Belief Two Weeks at a Time

Use the Sprint method – not just for products, but for yourself.

Your 2-Week Power Sprint:

• Weeks 1-2: Pick one crazy goal that moves you forward
• Every Morning: Ask “What will I do today that the old me would never try?”
• End of Sprint: Write down what happened when you acted bigger
• Look Back: What held you back? What pushed you forward?

Step 3: Show Your Crazy Ideas to Everyone

Most people hide their biggest dreams. That’s backwards.

Make It Visible:

• Share your wildest product ideas with your team
• Tell three people your huge career goal this week
• Put your daily “big thinking” tasks where everyone can see them

Here is Why…

Because when people say “that’s impossible,” you’ve found where the magic happens.

Step 4: Help Others to Help Yourself

Here’s the important part: The bigger you think, the more you need to help others.

As Jim Rohn said: “To get what you want, help others get what they want.”

For Products: Stop making features. Start changing lives. Ask: “How can this give users 10 times more than they expect?”

For Your Business: Stop competing on price. Start creating new categories. Ask: “How can we solve problems people don’t even know they have yet?”

For Your Career: Stop chasing titles. Start solving problems. Ask: “What problems can I fix that nobody else even sees?”

Leave Your Small-Thinking Zone (The Hard Part)

You can’t think big in a place that thinks small. Period.

This doesn’t mean ditching your friends. It means something harder but more powerful. It means finding groups where your “crazy” ideas are just Tuesday morning conversations. It means getting mentors who already did your “impossible” goal and now they’re bored and looking for the next thing. It means learning to smile and nod when someone says “be realistic”, then doing the opposite anyway.

Your 90-Day Upgrade

Start by joining one group where your biggest dream is their warm-up act. Maybe it’s an online community, maybe it’s a mastermind, maybe it’s just a Slack channel full of people who scare you a little with how big they think.

Then find someone two levels above where you want to be and talk to them every single week. Not to kiss up. Not to network. Just to absorb how they see the world. Because once you hear how a millionaire talks about money or how a VP talks about strategy, you can’t go back to thinking small.

Here’s the kicker: Each month, take one person who always tells you to “be realistic” and spend less time with them. Replace that time with someone who asks “why not bigger?” It sounds harsh, but your dreams are too important to let them die from a thousand cuts of “be careful.”

What Happens When You Think Big?

When I went from thinking small to thinking huge, my whole world flipped upside down.

My product went from barely getting noticed to becoming our company’s flagship in 18 months. Not because I worked harder, because I stopped asking “how can we improve this feature?” and started asking “what would make this unforgettable?”

I went from senior PM to director level in two years. Not because I played politics, because I stopped thinking like someone who executes plans and started thinking like someone who creates vision. Suddenly, I was getting pulled into strategy meetings I used to only hear about in hallway conversations.

But here’s the best part that nobody talks about: My team caught the bug too. Once they saw me swing for the fences, they started bringing me ideas that would have scared the old me. We became the team that other teams watched. We became the product that others copied. All because we decided that “realistic” was a dirty word.

But here’s the real secret: I stopped fixing small problems and started making whole problems disappear.

Your Monday Morning Game Plan

1. Before checking email tomorrow, write your biggest goal
2. Times it by 10 – yes, really
3. Find one person who already did it
4. Message them with one question
5. Start a 2-week sprint on one “impossible” task

The Choice You Have Right Now

You can read this, nod, and go back to your “safe” goals.

Or you can decide that “safe” is just another word for “boring.”

Rich people think big when they have nothing. Great products solve problems others won’t touch. Amazing careers break all the rules.

Your current money doesn’t matter. Your current job doesn’t matter. Your current numbers don’t matter.

What matters is how big you decide to think.

Ready to think bigger?

Join Dejan’s School and learn the three game-changing methods that turn big dreams into real results:

1. Sprint Your Way to Success – Break your impossible goal into 2-week power sprints. Test ideas fast, learn faster, and pivot before you waste time on the wrong path. This is how you make big thinking actually happen.
2. See Everything, Hide Nothing – Use transparent task boards that show exactly what matters most. When everyone sees the real priorities (including you), big goals stop feeling overwhelming and start feeling doable.
3. Build Your Dream Team – Stop waiting for permission. Learn how self-managed teams create magic through daily standups and peer power. When everyone owns the outcome, impossible becomes inevitable.

The only difference between you and people doing “impossible” things? They have a system that makes big thinking work.
Your system starts today.

Join Dejan’s School Now →

P.S. Think this is too crazy? Good. That’s where amazing things start. The question isn’t if you can think this big. It’s whether you can afford not to.