Let’s talk about something the financial advisor industry doesn’t want to acknowledge.
The “traditional” retirement planning advice—save 10%, buy a diversified index fund, and wait until you’re 65—hasn’t worked for most Americans since the 1990s.
It’s a playbook written for a different economic era.
If you are a high-income professional, a business owner, or in tech, you don’t just want to survive your golden years. You want optionality. You want the freedom to step away on your terms, not when a calendar says you’re “old enough.”
Retirement planning isn’t just about hoarding cash. It’s about engineering a strategy that compounds wealth while you sleep and minimizes the one thing that eats returns faster than a bear market: Taxes.
Here’s the uncomfortable truth about building a secure future, and how to actually get there.
Why Most “Plans” Fail
Retirement today isn’t a 10-year wind-down. It’s a 30-year or more active phase of life. With life expectancies pushing higher and healthcare costs exploding, relying on Social Security or a pension is a strategy built on hope, not math.
You need a strategy for:
- Financial Freedom: Not just paying bills, but doing what you want.
- Lifestyle Maintenance: Inflation is real. Your purchasing power is eroding every minute your money sits idle.
- Stress Reduction: Money problems in your 70s aren’t just stressful; they’re dangerous.
The goal isn’t just to retire. The goal is to detach your time from your money.
Savings Strategies: Move From “Saver” to “Owner”
Consistency is boring. It’s also the only thing that works. But high earners often fall into the trap of “lifestyle creep”—as income rises, spending rises to match it.
1. Maximize the Boring Stuff (Then Go Further)
Yes, max out your 401(k) and 403(b). That’s the baseline.
- Traditional: Lowers your taxable income today.
- Roth: You pay taxes now, but the growth is tax-free forever.
For 2025, the contribution limits are higher. If you are over 50, catch-up contributions are a no-brainer. But if you stop here, you’re just an average saver. Real wealth is built outside of these capped accounts.
2. Automate to Remove Emotion
Set up automatic transfers. You can’t spend what you don’t see. This forces you to live on the remainder, creating artificial scarcity that builds real discipline.
3. The “Raise” Rule
When you get a raise or a bonus, don’t upgrade your car. Upgrade your savings rate. If you can live on your current salary, bank 100% of the increase. This is how you compress decades of saving into a few years.
Investment Strategies: Stop Settling for Average
Here is where I disagree with almost every other CFP out there.
Most advisors tell you to own 500 different stocks to “diversify.” They slice the market into tiny, expensive pieces and call it safety. In reality, they are guaranteeing you average returns (minus their fees).
1. Concentration Builds Wealth; Diversification Preserves It
If you are in the accumulation phase, over-diversification is a drag on performance.
- The Wealthy Approach: Identify high-conviction opportunities—exceptional, founder-led businesses—and go deep.
- The Preservation Approach: Once you have made the money, then you diversify to keep it safe.
Don’t confuse the two.
2. Ignore the Noise
The market is manic-depressive. It loves AI one day and hates it the next. If you react to headlines, you lose. Basing your strategy on a long-term horizon (decades, not days) is the only way to win.
3. Growth Changes Everything
A 3% dividend on a flat stock isn’t building wealth—it’s financial melatonin. It puts your portfolio to sleep while inflation eats away at your purchasing power. We want businesses compounding at 15–20% (or more) a year. At that pace, your money has the potential to double every 3–5 years. That is the gap between “maybe retire at 65” and having real options in your 40s. “Safety” can often be the biggest risk you can take because it guarantees you won’t reach escape velocity.
4. Conviction Over Speculation
Before a dollar goes into the market, you need to answer a hard question: If this stock dropped 30% tomorrow, would you be excited to buy more, or desperate to get out? Most people treat stocks like lottery tickets. The wealthy treat them like business ownership. If you don’t have deep conviction in what you own, you will sell at the bottom every single time. You need to know exactly what you own, and why.
Tax Strategies: Keep What You Earn
It’s not what you make; it’s what you keep. Taxes are the single biggest expense over your lifetime.
1. Asset Location Matters
Treat your accounts like different buckets with different jobs:
- Tax-Deferred (Traditional 401k/IRA): This is your shield against today’s high tax brackets. Use this to reduce your taxable income right now, while you’re earning the most. The goal is to defer the tax bill until you can control the withdrawal rate—and the tax rate—in the future.
- Tax-Free (Roth): Put your highest growth assets here. We want the biggest winner to be tax-free.
- Taxable Brokerage: Use this for liquidity and tax-loss harvesting.
2. The Roth Conversion
If you have a low-income year (maybe you took a sabbatical or retired early), convert Traditional IRA money to Roth. You pay taxes at a lower rate now to avoid higher taxes later.
3. Tax-Loss Harvesting
This is the “free lunch” of investing. If you have a losing position in a taxable account, sell it to realize the loss. You can use that loss to offset gains elsewhere, lowering your tax bill. I do this for clients constantly—especially during market dips.
Retirement Income: The Exit Plan
Once the paycheck stops, the game changes. You need cash flow, not just net worth.
1. The 4% “Guideline”
The general rule of thumb is that you can withdraw 4% of your portfolio annually. But life isn’t a spreadsheet. If the market tanks the year you retire, you need to be flexible enough to cut spending so you don’t liquidate assets at the bottom.
2. Social Security Strategy
Delaying Social Security until age 70 guarantees an increase in your monthly benefit. It’s effectively an 8% guaranteed return for every year you wait. Unless you have health issues, waiting is usually the smart leverage play.
The Bottom Line
You can’t save your way to freedom if your strategy is average.
Avoiding common mistakes—like starting late, ignoring inflation, or being too scared to invest in growth—is the baseline. But if you want to have the potential to grow wealth exponentially—wealth that lasts and supports a legacy—you need to be intentional.
Stop playing by the rules written for employees. Start thinking like an owner.
Build the portfolio—and the life—you actually want.