This week, we walked through three very different retirement plans John Pierre, Tiger (not Woods), and James & his wife and each one had a different challenge: risk management, lifestyle creep, or navigating legacy wealth. I’ll take you through each, so you can see how we tackled their goals and avoided the most common pitfalls.

John Pierre: A Near-Retiree Without Bonds

Let’s start with John Pierre, age 61, and his wife, 58. They plan to retire in the next year or two and want to spend about $150,000 annually, with $80K for basic expenses and $50K for travel.

Their portfolio? Impressive:

• $2M in 401(k)s and IRAs
• $500K in Roth accounts
• $3M in brokerage
• $200K in cash
• Zero bond allocation

That last part? A red flag.

Joe and Big Al advised a 20–25% bond allocation—about $1.5M—to create a 10-year buffer of “safe money” during potential market downturns. That allows the rest of their portfolio to stay in equities for growth, but with a cushion to ride out the bad years.

We also talked about using municipal bonds in taxable accounts. They’re tax-efficient and can help smooth the process of Roth conversions, which we’re starting in 2025. Risk tolerance is critical here, especially if your gut tells you to sell during a downturn. Build your plan around how you actually behave, not how you wish you would.

Tiger (Not Woods): The Overconfident Millennial Millionaire

Tiger is 33, and he and his wife make $240,000 a year. Their numbers:

• $3.2M net worth
• $2M in brokerage
• $1M in pretax retirement
• $150K in Roth
• $375K in crypto
• $1M home with a 2.75% mortgage

He’s planning to retire when his taxable account hits $2.8M—and that’s excluding crypto. Add to that a potential $5 million inheritance, and you can imagine why Tiger feels like he’s winning the game.

But here’s the warning: overconfidence bias. Just because you hit it big once with a few stocks or crypto doesn’t mean that strategy will work forever.

Tiger wants to cut his retirement contributions, spend an extra $2,000/month, and lean into brokerage investments. Joe and Big Al hit the brakes. Inheritance is not a financial plan. And speculative returns are not predictable. The advice? Stay disciplined, keep saving, and don’t let lifestyle creep sabotage your future freedom.

James & His Wife: Rich in Assets, Not in Income—Yet

James and his wife, both 60, want to retire next year on $180,000 annually. Their portfolio:

• $2M in 401(k)s
• $2M in deferred compensation
• Purchased annuities with GLWBs (guaranteed lifetime withdrawal benefits)

They’ll get:

• $47K/year from annuities starting at 65
• $20K/year more from annuities starting at 74
• $50K/year in Social Security starting at 70

They’re also planning aggressive Roth conversions throughout their 60s to reduce the tax burden before RMDs (required minimum distributions) begin at 73.

Joe and Big Al offered a balanced take. They’re not the biggest fans of annuities (they usually benefit the insurance company more than you), but in this case, they work well as a bond substitute. That gives James room to take more risk with liquid assets to drive growth and liquidity for those planned conversions.

Why Delaying Social Security Matters

If you can afford to delay claiming Social Security, it can be one of the most powerful tools in your retirement plan. You gain 8% per year in delayed retirement credits plus COLA (cost-of-living adjustments).

But it’s not just about the math. Seeing your account balances drop in a market downturn while you delay withdrawals can be scary. That’s why Joe and Big Al always talk about Social Security as longevity insurance. You may not need the money at 62 but you might at 85. Plan accordingly.

Big Picture Advice

Here’s what all three scenarios had in common:

• Don’t rely on speculation or inheritance
• Keep a balanced asset allocation
• Know your true risk tolerance, especially once you stop working
• Avoid lifestyle creep your future self will thank you
• Make automated saving part of your plan so you don’t spend what you don’t see

We say this every week, but it’s worth repeating: retirement planning isn’t just about the numbers. It’s about behavior, discipline, and having the flexibility to adapt as life evolves.

Intended for educational purposes only. Opinions expressed are not intended as investment advice or to predict future performance. Past performance does not guarantee future results. Neither the information presented, nor any opinion expressed constitutes a solicitation for the purchase or sale of any security. Consult your financial professional before making any investment decisions. Opinions expressed are subject to change without notice.

IMPORTANT DISCLOSURES:

• Investment Advisory and Financial Planning Services are offered through Pure Financial Advisors, LLC. A Registered Investment Advisor.

• Pure Financial Advisors, LLC. does not offer tax or legal advice. Consult with a tax advisor or attorney regarding specific situations.

• Opinions expressed are subject to change without notice and are not intended as investment advice or to predict future performance.

• Investing involves risk including the potential loss of principal. No investment strategy can guarantee a profit or protect against loss in periods of declining values.

• All information is believed to be from reliable sources; however, we make no representation as to its completeness or accuracy.

• Intended for educational purposes only and are not intended as individualized advice or a guarantee that you will achieve a desired result. Before implementing any strategies discussed you should consult your tax and financial advisors.

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