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Contrarian Thinking

Comfort is Costing You

April 18, 2025
4 min read
Bird in a cage facing a dollar sign

The same instincts that keep you safe… are also keeping you small.

We call it Passive Ambition.

  • You crave freedom, but fear risk
  • You want all the upside, but avoid volatility
  • You dream big, but act small

Here’s the truth: Every builder you admire once looked like a fool.

Building anything meaningful starts with a bet, usually on yourself. No safety net. No guarantee. The world is mostly built by people who didn’t wait for permission — they just started. Even when it felt reckless. Especially when it felt lonely.

The scariest part is realizing no one’s coming to save you. But the best part is realizing you might not need them to.

That’s why we’re hell-bent on helping people will things into existence. Because we don’t want to settle for a world of this:

You the builders are this generation’s explorers, risk-takers, and adrenaline junkies. You do this because you’re wired differently. It’s hard, but that’s why you do it.

So today let’s talk about taking risks — why avoiding them entirely can cost you everything, and how to do it without losing your mind or wallet.

The #1 Way to Stay Stuck (Don’t Do This)

If you’re looking for a rock-solid plan to stay stuck where you are right now — financially, emotionally, professionally — look no further:

Step 1: Don’t Take Any Action

  • Do the minimum
  • Collect the paycheck
  • Let someone else decide your trajectory

Plenty of people build real wealth and ownership inside their W-2. They negotiate for equity. They invest their earnings. They stack skills and launch projects that make them indispensable.

But even then, if you’re just clocking in and out, never raising your hand, then you’re not working, you’re waiting. Waiting for “one day” — the most expensive day of the year.

Chart showing the rising cost of inaction over time

Step 2: Take Action You Barely Understand

Ambition without reason? That’s delusion:

  • You buy a business you’ve never seen
  • You jump at an investment you can’t explain
  • You leap with no strategy on how to land

Recklessness doesn’t make you bold. It makes you broke.

The Formula You Should Follow Instead

Take calculated risks. Smart risks. Risks you’ve studied, questioned, and prepared for.

Smart risk formula showing skill plus preparation times action

We think of risk in 3 levels:

  1. No Risk: Stagnation, safety, “one day” mindset
  2. Dumb Risk: FOMO bets, blind leaps, zero strategy
  3. Smart Risk: Studied, intentional, high-leverage moves

(Now is when you ask yourself, “Which type am I taking right now”?)

Every smart risk usually has 3 things behind it:

  • Context: You understand the terrain.
  • Conviction: You’ve done the work.
  • Contingency: You know you can come out alive if it goes sideways.

The guy who studies the numbers, learns the trade, buys the business, and lines up 3 recurring contracts before Day 1? That’s smart risk. The guy who burns his savings on an acquisition because “it sounds fun”? That’s dumb risk.

Ownership is the game and risk is the ticket. The key is not getting knocked the f*ck out, and that’s where focus comes in.

You Can’t Outwork a Lack of Focus

No matter how many hours you log, if you’re chasing everything, you’re catching nothing.

Sorry, it’s true. The ability to cut through the noise and lock in on what matters is the unsexy secret to winning. The cool part? Relentless focus often leads the haters along a very technical, very scientific curve that looks something like this…

Curve showing stages of envy as success grows

There’s a reason Facebook hit 3 billion users — and it’s not because “the website was good”. It was because they found their lever.

Early on, the team discovered that if a user added 7 friends within 10 days, they were hooked. So that became their focus. Their metric. Their move-the-world lever.

The best owners know how, when, and where to focus.

Archimedes famously said, “Give me a lever long enough and a fulcrum on which to place it, and I can move the world”.

Most business owners don’t know what their lever is. In a couple of weeks, we’re hosting an exclusive in-person business scaling workshop that will help you find it. Grab your seat here (while they last).

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1 Thing No One Wants to Admit

Relentless focus doesn’t eliminate risk, but it makes you calculated instead of blind. Here’s why that’s important for you right now…

Avoiding risk is increasingly a privilege of a world that no longer exists.

Inflation is mugging you at the grocery store, and AI is sharpening its knives for your role. In 2025, the only thing more dangerous than risk… is avoiding it entirely.

Passive Ambition thrives in times like these. It disguises hesitation as strategy and robs you of momentum. Don’t let this be you:

Dog surrounded by fire labeled with economic challenges saying “This is fine”

The key isn’t to avoid risks — it’s to take smarter ones.

The longer you wait, the bigger the bill.

Team Contrarian

The information contained here is educational, may not be typical, and does not guarantee returns. Background, education, effort, and application will affect your experience and the profitability of any business. Individual results may vary.

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