Tripp Yates

Founder, Eaglestrong Financial | CERTIFIED FINANCIAL PLANNER™ professional | CPA/PFS | Fee-Only Fiduciary Advisor | Isaiah 40:31

[Tripp Yates @trippyates]

Most people tend to think about taxes once a year, and only for that year.

Smart investors think about how their taxes might evolve over decades.

That's what good retirement income planning is all about.

[Tripp Yates @trippyates]

When people say they want to “protect their money,” it’s important to ask:

Protect it from what?

Market volatility or loss of purchasing power?

These are different risks.

Avoiding volatility may feel safe, but it’s usually temporary for diversified long-term investors.

However, if your money doesn’t grow enough to keep up with rising costs, that’s a lasting risk often overlooked.

Over decades, the risk of insufficient growth matters most.

If your portfolio can’t support your lifestyle over time, it has failed from the start.

[Tripp Yates @trippyates]

Work offers more than income.

It creates routine, a sense of contribution, and social interaction.

In retirement, these don’t automatically continue.

Retirement is most fulfilling when people engage in meaningful activities—such as hobbies, volunteering, learning, mentoring, or spending time with family.

Ending work is only part of the transition.

Designing a purposeful life after retirement is equally important.

[Tripp Yates @trippyates]

In financial planning, there is a key distinction:

Optimization focuses on achieving the best outcome based on current assumptions.

Optionality emphasizes flexibility for an uncertain future.

Some prioritize minimizing taxes.

Others value simplicity with fewer accounts and complexities.

Which approach is better?

It depends on the client.

Some aim to maximize every dollar.

Others choose simplicity, accepting potential trade-offs.

There are no wrong answers—just what matters most to you.

[Tripp Yates @trippyates]

Since 1937, the probability of a positive return in the S&P 500 has been:

53% over any single day.
77% over any single year.
93% over any five-year period.
97% over any 10-year stretch.

The point here is that it pays to be patient.

*Probability figures from First Trust.

[Tripp Yates @trippyates]

If you have access to a Health Savings Account and aren’t maxing it out, it’s important to understand what you might be missing.

The HSA offers a unique triple tax advantage: contributions are pre-tax, the funds grow tax-free (including investment growth), and withdrawals for qualified medical expenses are tax-free.

No other account—401(k), Roth, or otherwise—provides all three benefits.

To qualify, you must be enrolled in a high-deductible health plan (HDHP), not enrolled in Medicare, and not claimed as a dependent on another’s tax return.

For anyone planning for healthcare costs in retirement, the HSA merits serious consideration.

[Tripp Yates @trippyates]

Historically speaking, corporate profits have grown at roughly 8% per year.

At that rate, profits double about every nine years.

And over time, stock prices tend to follow profits.

So, is it any surprise that the market has historically doubled about once every 7-10 years?

It's not that the market is predictable. (It isn't!) It's that the direction of the next decade is (historically speaking) far more knowable than the direction of the next month — and that's the only timeframe that actually matters for building wealth.

Stop asking what happens next.

Start asking what will happen eventually.

[Tripp Yates @trippyates]

An important insight often overlooked by pre-retirees is that physical health may be the most critical factor in retirement well-being.

Health compounds over time; small differences early in retirement can lead to significant impacts over decades.

Retirees who prioritize exercise, sleep, nutrition, and stress management create a foundation that supports energy, mobility, cognitive function, and resilience.

Conversely, neglecting health can make the retirement lifestyle imagined more difficult, with increased physical limitations and reduced energy.

While genetics and circumstances play a role, controllable choices around activity, nutrition, sleep, and preventive care are among the most impactful decisions in retirement planning.

For pre-retirees, incorporating these health-related habits and the financial means to support them—such as gym memberships and medical care—into the financial plan is essential.

Building these habits during working years can compound into a significantly better retirement experience.

[Tripp Yates @trippyates]

When evaluating an investment, I ask:

“What does this asset produce?”

Gold, commodities, and cryptocurrencies produce nothing.

That doesn’t mean they lack value, but it means:

There’s no earnings stream to analyze or future cash flows to estimate.

Without these, there’s no clear way to determine their worth.

In contrast, businesses generate revenue, profits, and return capital to owners.

This provides a basis to evaluate their future and make informed long-term decisions.

[Tripp Yates @trippyates]

Volatility remains constant as your wealth grows, but your perception of it changes.

A 10% decline means $30,000 on $300,000, but $300,000 on $3 million—equivalent to the value of a house in some areas.

Markets move in percentages, yet we feel the impact in dollars.

If decisions are driven by dollar amounts rather than strategy, we risk abandoning the approach that built our wealth—the ultimate irony.

[Tripp Yates @trippyates]

If you knew that 74 out of the next 100 years would be positive — and that the up years would average more than 21% — how would that change the way you respond to the next bad headline?

Probably more than a little.

Now go look at the history of the last 100 years in the market, and you'll see that's exactly what happened.

[Tripp Yates @trippyates]

If you're early in your career or have children who are, consider this powerful yet simple savings strategy:

Each time you get a raise, allocate half of it to retirement savings.

This approach boosts your savings rate without reducing your take-home pay, allowing your savings to grow steadily throughout your career.

For young workers, this habit offers significant long-term benefits. Parents and grandparents can pass this valuable advice to the next generation.

[Tripp Yates @trippyates]

A simple investing observation:

The market often feels either too expensive or too risky.

Here’s why.

When markets rise:

1️⃣ Valuations seem high
2️⃣ Investors fear bubbles
3️⃣ Commentators predict corrections

When markets fall:

1️⃣ Recession concerns grow
2️⃣ Financial risks dominate headlines
3️⃣ Investors fear further losses

The market rarely feels comfortable.

Successful investing relies less on timing and more on discipline through uncertain times.

[Tripp Yates @trippyates]

Retiring early is often more challenging than expected, primarily due to healthcare costs.

Many are financially prepared and excited to retire, but the expense of health insurance before Medicare eligibility at 65 is frequently underestimated.

Options include COBRA, marketplace plans, spouse’s employer coverage, and health-sharing arrangements.

However, these options can be costly, and the best choice depends on your individual situation.

If you plan to retire before 65, address your healthcare coverage well in advance—don’t wait until after retirement to plan this crucial aspect.

[Tripp Yates @trippyates]

The mix matters more than the minutiae.

Benjamin Graham, John Bogle, and a 1986 study all show that 94% of long-term investment returns depend on asset allocation—not fund selection, market timing, or reacting to headlines.

Most investors focus on minor decisions instead of the key factor.

Your allocation drives your ability to retire comfortably, fund education, or leave a legacy.

It deserves greater attention than it typically receives.

[Tripp Yates @trippyates]

Do you think the world felt more or less certain in 1962 during the Cuban Missile Crisis, in 2001 after the Twin Towers fell, or in 2008 when the financial system nearly collapsed?

Each of those moments felt like uncertainty might be overwhelming.

Yet, as always, the market eventually regained stability.

Today's concerns are real, but uncertainty itself is not the risk—our response to it is.

Nassim Taleb describes antifragility: not just surviving disruption, but enduring it without irreversible mistakes.

This begins with a financial plan designed for real life, not an idealized world without surprises.

Because such a world is a dream, not reality.

[Tripp Yates @trippyates]

Not all dollars are considered equal at retirement because of how they are taxed.

- A dollar in a Traditional 401(k) or IRA gets taxed at ordinary income rates when withdrawn (except basis).
- A dollar in a Roth 401(k) or IRA comes out completely tax-free.
- A dollar in a Health Savings Account can come out tax-free for qualified medical expenses.
- And a dollar in a taxable brokerage account is taxed differently depending on whether it's interest, dividends, or capital gains (short-term or long-term).

Which means the account TYPE you save into during your working years can matter almost as much as the amount you save. Because the right mix offers the opportunity to tactically manage your tax bill each year in retirement, thereby potentially reducing your lifetime tax bill in the process.

[Tripp Yates @trippyates]

Since 1937, the S&P 500 has ended positive in approximately:

- 53% of single days,
- 78% of single years,
- 93% of five-year periods,
- 97% of ten-year periods.

Investor anxiety often focuses on short-term results, but most wealth is built over longer periods.

We encourage investors to focus on five- or ten-year horizons rather than weekly, monthly, or annual performance.

These longer timeframes better demonstrate the value of patience in investing.

Notably, most ten-year periods that ended positive did so by a significant margin, not just marginally.

Thus, a long-term perspective not only reduces the risk of loss but also increases the likelihood of substantial wealth accumulation.

Patience remains essential.

*Probability figures from First Trust.

[Tripp Yates @trippyates]

Over a 30-year retirement, inflation poses the greatest threat to a financial plan—not market crashes, volatility, or sequence-of-returns risk.

At a 3% annual inflation rate, a fixed income loses about half its purchasing power over 25 years; at 4%, it loses nearly two-thirds.

This underscores the importance of including assets in a retirement plan that historically keep pace with or exceed inflation.

Despite short-term volatility, equities or stocks have delivered long-term returns that surpass inflation across multi-decade periods.

Ensuring income keeps up with inflation is essential to sustaining financial needs throughout retirement.

Plan accordingly.

[Tripp Yates @trippyates]

Most investors think success comes from making many great decisions.

Charlie Munger would argue the opposite.

He would say that success mostly comes from avoiding bad ones.

Because a handful of poor decisions can outweigh years of good ones.