Why do high earners struggle to leave corporate life? (It's not what you might think.)

This is an irony that nobody talks about– the people best positioned to leave corporate life are often the ones most trapped by it. The six-figure salary, the fancy title, the golden handcuffs – they're all part of a cage built by success.

High earners have everything needed to start something new – savings, networks, experience. Yet they're often the last ones to make the leap. It's not about capability. It's about comfort.

I see this all the time. Senior executives with million-dollar ideas are stuck in jobs they've outgrown. Management consultants who dream of building their own companies, but can't pull away from the Partner track. These people often have every resource to succeed, except the one that matters most – freedom from their own success.

"The chains of habit are too light to be felt until they are too heavy to be broken."?

Corporate success creates chains that look like achievements. Each promotion, each bonus, each title becomes another reason to stay put.

The higher you climb, the harder it becomes to take that leap of faith. Not because the landing gets harder, but because the comfort gets deeper. The risks feel bigger.?

Do high earners make bad entrepreneurs?

"What do you do?" It's the first question at every dinner party. So, the further up the ladder you go, the more strongly your identity and job title become intertwined. That's the first psychological chain.

Think about introducing yourself without your corporate title. After years of being "Managing Director at Goldman" or "Partner at McKinsey," becoming "founder of a startup with a single employee" feels like a step down. It shouldn’t be, but it is.

It is about both identity and ego. When your business card opens doors, your LinkedIn profile attracts headhunters, and your title commands respect, walking away feels like erasing part of yourself.

"Your salary is a pay cheque; your title is who you think you are."?

That's the trap. We start believing our own PR.

Then there is the fear of public failure. It's one thing to fail quietly. It's another to fail when everyone's watching. And at senior levels, everyone is watching.

This is not just imposter syndrome, it's also a prison of perception. The higher you climb, the more you feel the pressure to maintain the image of success. Even if that success is slowly suffocating your dreams.

The money problem.

Money traps usually take the form of monthly payments. The fancy car, the premium postcode, the private schools - each one is another link in a chain keeping you tied to your corporate desk.

Here's how the trap works:

Your salary hits ￡250k. You upgrade your lifestyle. Nothing crazy, just "living well." Better schools for the kids. A nicer car. A bigger house. All sensible choices when you're earning well.

But then something interesting happens. These "upgrades" become necessities. Your lifestyle becomes a commitment.

The biggest luxury of wealth isn't buying things. It's buying freedom. But most people use their wealth to buy golden handcuffs instead.

The ironic correlation of wealth and risk.

You'd think that the wealthier you get, the more optionality you gain, but it's often the reverse. As your net worth grows, your risk tolerance shrinks. You start thinking about protecting what you have rather than building what could be. The same success that could fund your dreams becomes the reason you can't pursue them.

When you were fresh out of university with nothing to lose, starting a company seemed exciting. Now, with a comfortable nest egg, it feels terrifyingly risky. Your wealth has made you conservative.

The math might say you can afford to take the leap. Six months' savings, maybe a year. But your mind says something different. It says: "protect what you have."?

What will "they" say?

Success creates its own social gravity. When everyone in your circle is climbing the corporate ladder, choosing a different path feels like stepping off the earth. It's about belonging.

Then there's family. It's one thing to risk your own stability. It's another to risk your children's education or your family's lifestyle. Entrepreneurship suddenly feels selfish, even irresponsible. Are you prepared to sacrifice your family's security to pursue "your" dreams?

But here's the deeper trap – the idea of opportunity cost.

After years in corporate life, you've built specialised skills, industry knowledge, a professional edge. Walking away feels like throwing away years of investment.

Senior bankers worry their deal-making skills won't translate to their own company. Management consultants fear their presentation prowess won't matter in the real world. They're right... and wrong.

(The skills might change, but the thinking doesn't, and it's precisely that professional edge - that context - that makes senior professionals more likely to succeed than younger entrepreneurs. Which is a fact, by the way.)

Then, of course, there's FOMO.

That next promotion. The year-end bonus. The stock options that are about to vest.?

These aren't just external pressures. They're stories we tell ourselves to justify staying in our comfort zones.?

Remember, the same networks that keep you on track today could become your biggest supporters tomorrow. But first, you have to be willing to step off the treadmill.

How do you challenge your comfort zone?

There is a huge difference between comfort and happiness. That six-figure salary might keep you comfortable, but when was the last time it made you jump out of bed excited on a Monday morning?

Comfort is dangerous. It's like a warm bath - pleasant at first, then slowly cooling.

You stop growing. Stop dreaming. Start confusing a good pay cheque with a good life.

"I knew that if I failed I wouldn't regret that, but I knew the one thing I might regret is not trying." – Jeff Bezos

That's the real cost of comfort - the dreams you never chase.

Here's the ultimate irony– in chasing security, high earners often build their own prisons. The bigger the salary, the stronger the bars. The more secure the position, the less free you become to pursue what really matters.

But there's a way out.?

How to escape the rat race.

Start small, start now:

• Build a side project while keeping your day job
• Test your ideas without risking everything
• Use weekends to develop new skills

Audit your real needs:

• Calculate your actual monthly necessities
• Identify which luxuries you can live without
• Build a 'freedom fund' separate from your current lifestyle

Create a transition plan:

• Set a 12-month timeline
• Gradually reduce fixed costs
• Build relationships in your target industry before you need them

Reset your identity:

• Start introducing yourself without your title
• Network outside your corporate circle
• Find mentors who've made the leap

Build Your Runway:

• Save 6-12 months of essential expenses
• Maintain key relationships at your current job
• Create multiple income streams before leaving

The goal here isn't to abandon security. It's to redefine it.

Real security isn't about a pay cheque that goes away when your company downsizes. It's about being free to do what you want, when you want, with whomever you want. That doesn’t have to wait until retirement. It can start sooner than you might think.

The question is not whether you can afford to leave.

It's whether you can afford to stay.

Thanks for reading.

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