How to Become "Work Optional" | Chris Miles - The “Anti-Financial” Advisor

Here are the top 10 key takeaways from Scott D. Clary's conversation with Chris Miles, the "Anti-Financial Advisor," on how to achieve true financial freedom and become "work optional".

1. Traditional financial advice is often misleading

Chris Miles discovered that much of the traditional financial advice he once provided as an advisor was ineffective. His awakening came when he tried to advise his own father and realized that despite his father doing everything "right" according to conventional wisdom—maxing out his 401(k), getting employer matches, and paying off all debt—he would still run out of money within five to six years of retirement.

This revelation made Chris question the entire financial advising industry. He came to understand that most financial education comes from financial institutions that profit from people keeping their money in managed funds regardless of performance. This creates an inherent conflict of interest where advisors become pawns in a larger game designed to extract fees rather than create true financial freedom for clients.

2. Focus on cash flow, not accumulation

One of the fundamental shifts Chris advocates is moving from an accumulation mindset to a cash flow or acceleration mindset. The traditional approach of saving for decades to build a large nest egg often doesn't work because living off small withdrawal rates (3-4%) from investment accounts isn't enough for most people's retirement needs.

Instead, Chris recommends focusing on investments that generate consistent monthly cash flow. For example, he shared how he helped a client who had a rental property generating only $200 monthly profit (a 0.3% return on $700,000 of equity). By selling that property and reinvesting through a 1031 exchange into six properties in Louisiana, the client was able to generate over $8,000 monthly within five years—far more than what would have been achieved by simply paying off the original mortgage.

3. The "myth of the match" in 401(k) plans

Chris calls employer 401(k) matching a "myth of the match." While many financial advisors tout matching as a "100% return," the reality is more complex. This matching only applies to new contributions, not your entire portfolio, so the actual impact on your total return diminishes significantly over time.

He points out that if matching truly provided 100% returns consistently, people would become billionaires through their 401(k)s. Yet according to data he cited from Fidelity, only 1.8% of their 45 million account holders have achieved even $1 million in their accounts. Furthermore, 35% of those millionaires still don't believe they have enough to retire, suggesting that even with matching, these plans aren't creating true financial independence for the vast majority of people.

4. The 4% rule is outdated and dangerous

The commonly cited "4% rule" for retirement withdrawals (the idea that you can safely withdraw 4% of your portfolio annually without depleting it) is based on historical data from 1926-1976. Chris points out that this period preceded significant economic changes like abandoning the gold standard in 1974, which led to higher inflation rates.

With people living longer and facing persistent inflation, Chris suggests that 3% is a more realistic withdrawal rate for those retiring in their 60s. For those seeking early retirement (in their 30s or 40s), he recommends an even more conservative 2% withdrawal rate. This significantly changes the calculation of how much you need to save—potentially doubling or tripling the required nest egg compared to what many financial advisors suggest.

5. Real business ownership and real estate are superior wealth-building tools

Chris observed that even financial personalities who recommend mutual funds and stocks often build their own wealth primarily through business ownership and real estate. He specifically points to Dave Ramsey, who despite advising others to invest in mutual funds, reportedly has his own wealth concentrated in his business (approximately $50 million) and real estate holdings (approximately $150 million), with minimal investments in the stock market.

This disconnect between what financial gurus recommend and how they actually build wealth represents a crucial insight. Chris argues that business ownership gives you control over your income and growth potential, while real estate provides tangible assets that can generate cash flow and appreciate over time. Both avenues offer advantages that traditional stock market investing through retirement accounts cannot match.

6. Value creation is the foundation of wealth

Chris emphasizes that the most reliable path to wealth is not focusing on how to make more money, but rather on how to create more value for more people. Money follows when you solve problems and serve others effectively. This mindset shift transforms money from something you chase to something that naturally flows to you as a byproduct of the value you provide.

This principle applies whether you're a business owner or employee. For employees, it means focusing on how to create more value for your employer to earn raises and advancement. For entrepreneurs, it means developing products or services that genuinely improve customers' lives. When value creation becomes your focus, wealth becomes more formulaic and less dependent on luck or timing.

7. The retirement landscape has fundamentally changed

The podcast highlights how drastically retirement planning has changed across generations. Previous generations often had defined benefit pensions, guaranteeing income for life. Today, most workers only have access to defined contribution plans like 401(k)s, shifting all the investment risk to individuals rather than employers.

This shift has created a significant gap in retirement security that traditional financial advisors attempt to fill, but often with inadequate solutions. Without pensions, today's workers face much greater uncertainty and need different strategies than their parents used. Many following the conventional path of saving in tax-deferred accounts may find themselves working well past traditional retirement age simply because these vehicles don't generate sufficient income.

8. Passive income requires strategic control

Chris distinguishes between active and passive investing, emphasizing that true financial freedom comes from creating passive income streams. However, he cautions that being "passive" doesn't mean abdicating control or understanding. Instead, it means strategically positioning yourself where you maintain oversight while minimizing daily operational involvement.

In real estate, this might mean hiring property managers while maintaining ownership, or lending money to experienced operators rather than doing all the work yourself. Chris acknowledges he's not a good property manager, so he partners with experts in this area. Similarly, with raw land investments, he finances deals while partners handle acquisitions and sales. This approach allows him to leverage others' expertise while maintaining control of his capital.

9. Partner selection is critical for investment success

When investing passively with others, Chris emphasizes the importance of rigorous vetting. He looks for operators with experience through full market cycles (preferably pre-2010), consistent focus on specific niches rather than jumping between investment types, and personal financial stability. He's wary of people who pivot from one investment type to another without deep expertise.

Chris also values operators who put their own money into deals and maintain healthy cash reserves. One positive indicator he mentioned is when someone is willing to pause operations rather than chase deals that don't meet their established criteria. This disciplined approach to partnerships has helped him avoid many problematic investments and find reliable operators in various niches.

10. People are the true assets, not things

Perhaps the most profound takeaway from Chris's interview is his perspective that people, not possessions or financial assets, are what truly matter. He explains that material things only have value because people assign value to them. Without human relationships and impact, wealth becomes meaningless.

Chris frames financial success as a stewardship responsibility. We arrive with nothing, depart with nothing, and in between we're entrusted with resources, time, and talents to use wisely. This perspective shifts the purpose of wealth creation from accumulation for its own sake to using resources to create positive impact in others' lives. Success then becomes measured not just by financial metrics but by the legacy of service and value creation left behind.