Why High Earners Stay Broke (And How to Escape the Trap) | Chris Miles

Making six figures but still feeling broke? You’re not alone. In this episode of Executive Connect, financial freedom expert Chris Miles reveals why so many high-income professionals are secretly trapped in what he calls the “High Income Hamster Wheel.” He explains how traditional financial advice like saving more, paying off debt, and maxing out your 401(k) actually keeps you stuck and broke, and what to do instead.

Chris shares his story of going from over a million dollars in debt to retiring twice before 40, and the counterintuitive strategies he used to escape the trap by focusing on cash flow, liquidity, and passive income over accumulation. If you’re tired of feeling like your high salary still isn’t enough, this episode will show you how to build true financial freedom and live life on your terms.

Timestamps:
00:00 The moment that changed Chris Miles’ entire view of money
02:45 Why traditional financial advice keeps you broke
05:10 How Chris went from debt to financial independence twice before 40
07:42 The trap of being asset rich but cash poor
10:33 Why your 401(k) and IRA might be your biggest mistake
13:02 What it really means to make your money work for you
15:40 How high earners can lose everything by locking away their money
18:04 Why your financial advisor doesn’t want you to retire early
21:19 The biggest myths about saving, risk, and returns
25:11 What wealthy people do differently with their money
28:36 Turning equity into income, a smarter way to think about your home
31:50 Real examples of clients who replaced income with passive cash flow
35:24 Why boring investments are often the most profitable
38:03 The mindset shift from saving for retirement to building freedom
41:26 How to rewire your financial beliefs and stop chasing income
44:18 Final advice, know your why and design wealth around it

Key Themes:

• Financial freedom vs. high income

• Cash flow over accumulation

• Passive income strategies

• Escaping traditional financial advice

• Liquidity, leverage, and control

• Rethinking retirement planning

• How wealthy people think differently

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